MASS WHOLE


A desperate father on a COVID odyssey

NOTE: The mobile site kinda stinks; it stacks the three columns instead of displaying them in rows, so the towns are out of order. Keep scrolling, I promise you’re there. I’ve spent most of my life in Massachusetts. Through moving around and coaching high school sports, I’ve seen a good chunk of it, but there are still corners I haven’t experienced. When I realized that COVID-19 was going to rob me of my normal summer plans, I set out on a mission: to touch every town in Massachusetts that I haven’t yet visited. This is not an exhaustive survey of each town, even the ones I know well. It’s just one man’s take on a brief encounter with each of the Commonwealth’s 351 municipalities. My two sons are along for most of the ride.

  • – I don’t do “borough”, I do “boro”. If you have a problem with that, your hometown will become “burro”
  • – Until I figure out how to add subpages without screwing up the layout here further, you can find my “best of” lists at the bottom of this page.
Abington – There’s only one time I’ve been to Abington on purpose. Barrett’s does a pretty serious haunted house every year, and I went with my now wife when we had been dating for six months. It’s one of those deals where you enter a room and there’s an empty surgery table covered with blood and you know some actor made up like a deranged amputee is going to grab your leg or something. Anyway, when my wife asked me what I was doing, I told her that I was making sure no one attacked us from the rear. She didn’t buy it. Good place to grab dinner next door at the Abington Ale House.

Acton – The Discovery Museum is awesome. In pre-COVID times, it was a go-to for entertaining the kids. I particularly loved the treehouses outside. My oldest also dumped a measuring cup of water on a random kid at the water table, but that’s neither here nor there.
Acushnet – The ruins of the White Factory gave my sons a new place of wonder and mystery where they could eat snow off the ground.
Adams – Here’s Griff as the tallest toddler in the Commonwealth. We drove to the top of Mt. Greylock, the state’s highest peak, and ascended the War Memorial Monument to see five states at once. Further down the mountain, we tried to take a dip at Peck’s Falls, forgetting that some mountain streams are still frigid even in August.
Agawam – Look at that damn sub. 18 inches of Italian deli joy. Pajer Superette is not for the faint of heart. Unfortunately, Agawam also failed the Random Town Scratchy Corollary (see Grafton).
Alford – Here’s how Alford describes themselves on their town website: “Alford does not have a post office… Our town has no stores, no motels or hotels, and not a single gas station…” So we were hard-pressed to find anything to do. All my research churned up was that the marble for New York City’s City Hall was harvested from a now defunct quarry in Alford. I asked my boys if they wanted “to get out and run around, bringing joy and mirth to this woefully dull town.” The one who can talk said “No.” Okay. Moving on…
Andover – What it lacks in space, it makes up for in tradition: Coming in at over two centuries old, the Andover Bookstore is the oldest independent bookstore in the country. Despite it’s small size, it had a wonderfully diverse selection.
Ashburnham – The family hiked up Mount Watatic, which entailed some steep, rocky sections, lovely panoramic views (you can see Boston), and a wood bridge over an overflowing pond that is difficult to cross with a three year old on your shoulders. Big highlight: my son peed in the woods for the first time! Big day! (potty training is brutal)
Ashland – I miss The Corner Pub. The place was like the wild west. You could sit up in the balcony and watch locals go at it. Also, I once ran into one of my high school football coaches there, and he had no idea who I was. It’s now a Mexican restaurant.
Auburn – I’m a flavored coffee guy, but there is something to be said for a regular cup of diner coffee, which I picked up at Heritage Coffee Shop before hopping back on the highway. I also discovered an Arby’s here, which to this point, I thought was just a theory and not a real place.
Barnstable – I’ve been here for a number of random reasons – Cape Cod Mall with my grandmother, Chick-fil-a, ferrying a bunch of wealthy older guys to the now-defunct Hooters for my summer job…but none of it is that interesting, so instead, can we talk about who the heck does Barnstable think it is claiming like 11 villages or whatever it is? Centerville, Osterville, Marston Mills…the list goes on, all in a town of less than 50,000 people. Get over yourself, Barnstable.
Bedford – Keegan and I hiked to Two Brothers Rock, an isolated riverside park in the Altman Conservation Land, for a post-Easter egg hunt. Unbeknownst to him, there is one last egg on top of the rock commemorating Governor Winthrop behind him, and also unbeknownst to him, that egg contains a piece of string. Again, post-Easter…slim pickings.
Belmont – One summer, I worked for a moving company. We did a job in Belmont where we had to move a family from one side of a neighborhood to the other. In an effort to save money, the woman who booked us lied about having an entire garage that needed to be emptied, thinking she could “oh, by the way” sweep it past us, but the end result was just that we were short staffed and were stuck in Belmont for 14 hours, in 90 degree heat, for no tip. I don’t know her, but I still don’t like her.
Bernardston – Gorgeous area. Got the best cup of cold brew coffee I’ve ever had at Sweet Lucy’s bakery, but I need to go back and explore the area some more.
Blackstone – Blackstone Gorge looks unassuming from the parking lot, but there’s an easy, scenic trail that crosses into Rhode Island as it follows the river.
Boston – I’ve heard of it. I lived in Brighton and worked in West Roxbury, though I don’t know if either qualify as capital-B Boston. The changeover for many of my old haunts makes me sad, but perhaps the place I miss the most was Pic-a-Pasta. It was a “build your own pasta bowl” takeout place in Oak Square that I was frequenting even when my bank account was in the double digits because even though I was a 23 year old camp counselor, I refused to suffer further (more practical) embarrassment by moving back in with my parents. If you’re coming in from out of town, my advice is to avoid Fanueil Hall and Quincy Market because they’re overpriced tourist traps. I also would advise not coming in from out of town at all because there is a damn pandemic afoot.
Boxford – We stopped at the Boxford Community Store for a slice of pizza. It wasn’t remarkable, but the staff couldn’t have been more friendly and the outdoor seating was a big draw for the locals.
Brewster – I grew up spending the summer down here and my parents live there permanently now. It’s quieter than some of its neighbors in the summer in a good way. My favorite thing about Brewster might be the homemade cookies from Ferretti’s Market.
Brockton – Brack’s, a sports bar with a Portuguese flare, might have the biggest bar I’ve ever seen. I had to look up the word for a ten-sided object – a decagon. The Portuguese came through in my stuffed quahog, which was delicious with a kick.
Buckland – I feel a little bit bad about Buckland. You stand there, looking across the river at Shelburne Falls, thinking, “my, what a lovely little town”, then you turn around and see Buckland’s sugar cube town hall surrounded by not much else. Buckland is the Jan Brady of Nowhere West.
Canton – Thought process: I’ve been here, right? (checks map) Ugh, Trillium. Overcrowded, weak food options, and mediocre beverages. Overrated. Check, please.
Charlemont – We’ll need to come back to check out the Thunder Coaster, but at first blush, Charlemont was a little too touristy. That the statue built to commemorate the Mohawk tribe is adjacent to a cheesy campground is a microcosm. Tried to buy a slice in town, but it was closed, so I settled for yet another losing lottery ticket.
Chelmsford – Tucked away on a lazy river in North Chelmsford is The Establishment, which had one of the coolest aesthetics I’ve come across (and at this point, I’ve seen a lot of mills-turned-restaurants.)
Chester – This is going to sound more negative than I mean for it to, but Goldmine Brook Falls were disappointing, I ended up on a dirt road that I wasn’t sure I’d ever emerge from, and I’m pretty sure the guy who swiped my card at the bar where I bought two slices of pizza perpetrated some credit card fraud against me. Okay, maybe I mean it.
Chilmark – I’ll try not to make assumptions about the clientele I encountered at Menemsha. But someone’s willing to spend $3 on those cans of purified water, and it ain’t me. The beach itself was a hidden gem, if such a thing is possible on the Vineyard.
Cohasset – Visited here for the first time during COVID, and I have to say, the seaside mansions along Atlantic Avenue rival anything I’ve seen anywhere else in the state, including the Cape.
Conway – The picture above was taken at the Bardwell’s Ferry Bridge, but what’s more exciting is that Conway is the home to the graves of both Jack Chesbro, who holds the MLB record for wins by a pitcher in a season at 41, and 3x Pulitzer Prize Winning Poet Archibald MacLeish.
Danvers – Nothing says “luxury condos” like a former insane asylum where the horror stories of early 20th century patient treatment are legendary. Then again, who am I to judge? Had my kids not been napping, I was ready to hike them down to the patient graveyard. We also visited America’s oldest cultivated fruit tree (it’s in a hospital parking lot) and the Cookie Monstah food truck (delectable.)
Deerfield – The Rock, Fossil and Dinosaur Shop is a little roadside attraction that offered the boys a chance to “dig for treasure” and crack open a geode. We also got lunch and a few drinks at the Berkshire Brewery, where they went out of their way to cater to our kids with chalk and bubbles.
Douglas – If you pass through Douglas, just over the state line into Thompson, CT and go for a stroll down the Air Line State Park trail, you’ll come back into Douglas at the Tri-State Marker, where CT, RI, and MA meet. Douglas State Forest is also a pretty scenic place to take a walk, parts of which are stroller friendly.
Dudley – I took my kids for a walk in Pierpont Meadows, which ended up being another classic game of “No stroller, I want to walk, just kidding, now I’m going to sit in this dirt for ten minutes”
East Bridgewater – I went to a wedding at The Villa where my wife was a bridesmaid and I knew nobody else, which translated into me murdering the mashed potato bar five times over.
Eastham – The Fort Hill Trail passes from grassy fields overlooking salt water marshes to a mile long boardwalk that weaves through a swamp.
Edgartown – Went to the beach here once with friends from Connecticut, and was amazed at how warm the water was compared to its counterparts across the water on the Cape. And of course, drove over the Jaws Bridge, too.
Essex – Stopped in at Woodman’s for lunch. Very crisp fried food. No, I did not get “chocolate wasted” a la Grown Ups, which was filmed there.
Fall River – Took Keegan to Battleship Cove for the day and he was obsessed with exploring the trio of ships and the submarine docked there.
Florida – We stumbled upon the eastern terminus of the Hoosac Tunnel, one of the state’s most infamous locations for the supernatural. A five-mile-long tunnel through the Berkshires, it was dubbed “The Bloody Pit” after almost 200 workers perished during its construction. We couldn’t go past this point because it’s still an active railway, oh, and it’d be messed up to take a one-year-old into a pitch-black haunted train tunnel.
Franklin – Perhaps our favorite dinner spot right now is in Franklin, the Alumni Cafe. Family oriented enough that it’s not sketchy we bring our kids with us, but adult enough that it still kind of feels like a night out. Above is DelCarte Playground.
Georgetown – If you’ve ever driven to Maine from Boston, you’ve passed under the Pingree Farm Rd Bridge, no longer driveable as it is now a part of Georgetown-Rowley State Forest. The picnic above was soon interrupted by two women with their dogs not on leashes legit eating half of Keegan’s meatballs out of his lunch. I’m not the “put your dogs on a leash!” taskmaster, but if you have so little control over them that they steal my kid’s lunch, you’re getting the dirtiest glare I can muster.
Goshen – Picture the Emerald City in The Return to Oz, but with a sacrificial alter, and that’s the Three Sisters’ Sanctuary. I’m partially kidding – containing an array of always interesting and sometimes creepy metal and stone sculptures, the sanctuary was a fun place for the kids to explore, complete with a a fire breathing metal dragon.
Granby – This place is absurd. There are claims on the internet that the oldest meteorite on earth can be found here, yet you can’t find marketing for it anywhere. When I asked someone in the know, they said it was one of those field trips you take in the second grade that even then your teacher is telling you it’s a fib. They could at least play it up more. Do better, Granby.
Greenfield – Really scenic western suburb. Doesn’t make you feel like you’re in the middle of nowhere. We climbed Poet’s Seat Tower and the view was outstanding.
Hadley – I wish I had more time to scrounge through the stacks at Grey Matter Books, a bookstore hidden in the basement of an old mill along the rail trail that boasts both vintage and brand new titles.
Hampden – We had Memorial Park playground to ourselves. I particularly liked the old school “log cabin” style wooden playground they still had in good condition. Oh, and moments after this picture, Griffen missed a step and wiped out.
Hanson – A lot of people have grown in really inspiring ways over the pandemic; I’ve just gotten really into Coffee Oreo ice cream. There’s a careful balance to the flavor – some aren’t coffee enough, or are devoid of oreo chunks. Heidi’s Hollow in Hanson nailed it.
Harwich – I attended a lot of Cape League baseball games here growing up, and one of my family’s favorite restaurants in the area is the 400 East. Above, I attacked my mom with an inflatable shark at the Harwich Stop n’ Shop.
Hawley – We started our day at the Beehive Kiln. I’m still not totally sure what a kiln like this did, but it’s a cool structure that’s fully intact and approximately 15 degrees cooler than outside.
Hinsdale – Hinsdale had a little bit more going on than some of its neighboring counterparts. We picked up lunch from the Hinsdale Trading Company, which had a pretty diverse menu for your local general store-type place, AND finally passed the “random town scratchy corollary” when we hit for $100 on a $10 scratchy.
Holland – It feels blasphemous to get a burger at a seafood restaurant, but that’s just what I was in the mood for. I will say that the quality was quite good, and I would suspend my previous assertion about trusting seafood west of Worcester next time I am in the area (so probably never.)
Hopedale – An underrated town perhaps because it is so small. Beyond Full, located in the town hall, creates some of the wildest milkshakes you’ve ever seen. Made for a great little outing with my eldest.
Hudson – New City Creamery makes great ice cream, and the Horeshoe Pub is a good local joint. Both are located adjacent to the bike path. There’s also a much crustier local bar across from the Horseshoe where everyone gave us dirty looks just for walking in, but I had the last laugh. I accessed their jukebox from the parking lot using an app and made sure they listened to all the Spice Girls they could handle.
Ipswich – Took the kids to Castle Hill at the Crane Estate. “Look guys! A castle!” “Daddy, I found a rock.” “Look guys! you can see the ocean! Daddy, I found sand.” “Look guys! Atlantis is rising from the depths!” “Daddy, I found a pine cone.”
Lancaster – The Atherton Bridge turned 150 years old this year only to be damaged by a flash flood in April, making it now impassable.
Lee – Quintessential “charming main street” alert. I bet they hate all the New Yorkers in the summer and fall, and, if we’re being honest, people like me, too. I got a coffee from Prado’s.
Leominster – It’s too difficult to pick just one weird monument in Leominster, so I give you both the birthplace of Johnny Appleseed, and the grave of Joseph Palmer, who was murdered for having a beard. The circle of life, all right here, in Leominster.
Leyden – So, there’s the covered bridge above that marks the border with Greenfield, and there may be a butcher shop in town, but it vanished from my GPS mysteriously mid-route. Not a great sign, Leyden.
Longmeadow – First, we got an everything bagel from Alex’s Bagel Shop, and I rate it an A-. Not the best ever, but if I lived nearby, I would frequent the place. Then we hit up the Bliss Park playground, featuring our old friend Mr. Potatohead, or as my son creepily calls it “the body”, as in “Look, Dada, I have the body and its eyes and its ears and its mouth.”
Lunenberg – We went to Whalom Park a bunch of times growing up, and now they’ve turned it into a housing development. That was a piece of my childhood and they destroyed it. Now, that’s why I am the way I am.
Malden – I’ve been to Malden for a number of reasons, and I must say the Shanghai Moon is strangely calling me to return. Above is the moving company where I worked for one grueling summer.
Marblehead – I’ve been here once for a kid’s birthday party. Above is Devereaux Beach during the winter.
Marshfield – My wife’s family goes to Brant Rock every summer, and our main two spots are the Venus and Haddad’s. I get the sense most people who prefer Haddad’s, and I get it, different vibe, but personally, the Venus is more my speed. One of those places that now signifies summer to me. I also once ordered a sundae for dessert at Mamma Mia’s and it came in a massive martini glass with four spoons like the Ziggy Piggy in Bill and Ted, and my father-in-law reminds me of it every summer.
Maynard – There is a nice bike trail that runs through the center of town past an old mill that has been converted into contemporary office space over a pond.
Medway – Want to see two kids you went to high school with get in a fight in a parking lot? Hit up the Medway Lotus. I took my wife here on our third date (what?) and we watched two guys do karaoke to “What’s the Difference?” by Dre and Eminem, except they only knew the one lyric, and mumbled the rest of the song. To end on a brighter note, I think of Medway as having the best one-two punch for cheap kids entertainment – the indoor playgym at Tumblebeans that also has a coffee shop, and the playground at Choate Park.
Merrimac – I’m with you; it’s time Merrimacport stop lying to itself. You’re a small neighborhood on the state’s third largest river – “port” is a stretch. Apropos of that, Merrimac Games and Collectibles had a wide array of classic video games and knowledgeable staff.
Middlefield – Before I went here, I mocked how generic the town name was, but there are two unique destinations worth seeing. The first is the Keystone Arch Bridge Trail, an easy to navigate walking trail that weaves around the old archways of the railroad and the Westfield River. The other is Glendale Falls, the perfect place to take a dip in a stream while also seeing some cool waterfalls that descend 160 feet down a series of ledges.
Millbury – The Chicken and Waffles from The Coop were solid, but the succulent scents wafting out of this place tell me there’s a lot more there worth uncovering upon a return visit.
Milton – So we were hiking Blue Hills, and we were looking to get back to the car the fastest way possible. We look at the map, and we’re like “oh, this trail looks shortest.” What we didn’t pay attention to is that while the footage was shorter, it was all straight up and down. Reading topography is a lost art.
Montague – We spent the day here as a family – did a stroll along the canalwalk, grabbed lunch in Turner Falls, and paid a visit to the Montague Book Mill, where I could’ve spent four more hours hanging around between the books, food, and scenery.
Mount Washington – Of course, we tackled Bash Bish, the state’s largest waterfalls. Unfortunately, the Massachusetts lot was closed, so we had to drive a mile down the road and enter from New York. This made the hike about 3x longer, but still manageable, and we didn’t drive all this way to turn around. The trail was crowded on a Monday morning, and if you’re a stickler for people following social distancing protocols, this is not the place for you.
Natick – Lookout Farm is a wildly popular fall destination for food, drinks, and picking various objects. I do not support the many overhauls of the Natick Collection/Mall/Atrocity – they should’ve quit while they were ahead and just let it bathe in the Wonder Bread factory aroma forever.
New Bedford – I have two recommendations here – one, the Whaler’s Tavern for casual seafood and drinks, and two, The Donut Factory for donuts so opulent you’re afraid to bite into however many 1000 calories might be inside. They even have a drive thru, despite everything being made to order from scratch.
New Salem – The Bear’s Den is such a cool and easily accessible waterfall that it’s worth the trip alone. We also paid a visit to Joyce at Quabbin Sky Vineyards, where she has set up part of her home as a wine tasting room.
Newton – Cabot’s is, without a doubt, the go-to diner/ice cream shop experience in the Greater Boston area. Their sundaes could crush a buffalo.
North Andover – Some of my favorite wrestling memories have occurred in this gym, but today I took a stroll around Weir Hill, a small network of trails wedged behind Stevens Pond.
North Reading – Now is as good of a time as any to talk about vanity street signs – you know, the towns that diverge from the standard green and white. The best are Weymouth’s, with the maroon and white letters, and the second worst are here in North Reading. I know green and yellow are their school colors (not to mention my town’s school colors as well) but they look weird on street signs and I imagine the lack of contrast would make them harder to read at night. Which town is the worst? Norfolk, with those weird picket fence posts with vertical vinyl letters.
Northbridge – Took a stroll along the Mumford Riverwalk on a brisk fall day, which was only made more pleasant by…two random guys whittling bowls from scratch? Okay.
Norwell – Gaffield Park has a sweet modern playground set back off the road surrounded by a forest. My pale complexion always appreciates a lot of shade, and the boys enjoyed the abnormally tall slides.
Oakham – When they tell you Sampson’s Pebble is easy to locate, they are lying. To be fair, I’m positive we did not enter the Mid-State Trail at the right spot, and to be more fair, we would’ve gotten there much faster if SOMEONE didn’t rip a leaf off of EVERY SINGLE FERN IN THE DAMN FOREST.
Otis -Above is the very top of the well-hidden Otis Falls, located just below the Otis Reservoir. One of my favorite random things about the Mass Pike is when you hit Otis, you can already see the sign that says “Entering Becket”. Then, 1000 feet later, is ANOTHER sign saying “Entering Otis”. So you’re in Becket for like 5 seconds. I like to imagine some petty rivalry between the two towns where Becket was like “We can’t let Otis hog the spotlight!” Every time we drive past this, I point it out to my wife, and she has yet to care.
Paxton – Moore State Park is a fantastic place to take small kids. The waterfalls and mill are accessible by stroller all the way from the parking lot, there are five or so waterfalls to check out, and a small trail lined with flowers. It was great right until my three year old stabbed me in the face with a branch, causing me to let out an expletive that probably scared some nearby strangers.
Pembroke – The Lucky Dawg Pub has a great patio on a lake that they let us use for a private party. As of the summer of 2020, they’ve added a giant treehouse behind this patio that is an unreal spot for drinks and dinner in the summer.
Petersham – “Petersham” comes from the ancient Celtic word for “the place where cell reception goes to die”. We did the Swift River Reservation hike through the Slab City portion, and while the quarry and the picnic at the cottage foundation were lovely, this was not a delightful walk when you have a three year old who isn’t willing to walk by himself.
Plainfield – It’s plain. It’s a field. It’s a Plainfield. Update: Now that I’ve been here, I don’t have much to add. I did make the mistake of not planning ahead for the one venture we looked into – looking for Manganese at the old Betts Mine (because what kids don’t love Manganese?) It’s my own fault for not booking in advance as their website states.
Princeton – Ambitious young father that I am, I decided to take my boys to the Crow Hill Ledges at the Leominster State Forest. As cool as watching people rock climb a vertical face was, it was a traumatic journey up 200 stairs and along a narrow ledge for a father of two kids too young to use a potty.
Randolph – We had Imagination Station Playground to ourselves after a fresh rain and finally sampled one of the most hallowed bar pizzas near the south shore at the Lynwood Cafe. It was much better than the “ice cream and hot dogs” Griff served me at the playground, AKA wet mulch.
Rehoboth – “Where’d you take the kids today?” “A giant haunted rock where King Philip’s War ended and the spirits of those lost linger to this day. But Keegan did a great job climbing!”
Rochester – Realtor, probably: “So the good news is that there’s new kitchen counters, hardwood floors, new furnace…” Prospective Buyer: “Is there a catch?” Realtor: “Well, there is a giant haunted boulder on the property with a witch painted on it that you can supposedly here the whispers of the dead in its crevices.” I wanted to take the boys for their first frappes at Captain Bonney’s across the street from Witch Rock, but they were closed for the season.
Rowe – Nothing says father-son bonding like a decommissioned nuclear power plant. Seriously, though, my father regularly made trips to Rowe over his years working for Yankee Atomic, so it was neat to bring his grandson here to what is now a forgotten monument to the late 20th century.
Russell – We all have our food quirks, and after visiting The Breadbasket, mine is now that I will no longer eat bread that wasn’t fresh baked that morning by Mennonites.
Salisbury – Salisbury Beach is a little too touristy for me, but they have yard games, fried dough, and of course, the old carousel. They tout their boardwalk pizza, so I got a slice at Christy’s.
Saugus – So I finally made it to the Kowloon, though admittedly I was there at noon for a place with strong 1 AM vibes. Better than average pork fried rice.
Seekonk – I stopped for lunch at Provolone’s Italian Deli. The pizza slice was really good – New York style thin crust that’s hard to find around here. The steak and cheese wasn’t quite as good, but still solid.
Shelburne – Shelburne was the first Western Mass town that sparked the thought, “If I ever had to hide out from everyone for awhile, this would be a good place to do it.” I mean that it’s bucolic without being depressing. Not sure what I’m getting into that would require going on the lam. The Bridge of Flowers and glacial potholes are obvious; definitely get a coffee from Mocha Maya’s.
Shrewsbury – I went on a date in Shrewsbury once with a girl I met at college. I don’t want to assail love not lost, but she once AIMed me seven times while I had the same away message up about playing softball. The last one said, “WHY ARE YOU IGNORING ME?!?!” Above is Ski Ward, and even though people made jokes about how small it was at the time, it was a great place to learn how to ski.
Somerville – I spent a memorable New Year’s Eve at The Burren. It involved a friend snapping their flip phone in half. I also have some great memories of watching the Bruins ’11 Cup run at Joshua Tree across the street.
Southboro – I once took a date to Tomasso because she was 22 and I was 27 and I felt the need to prove that I knew how adults were supposed to go on dates, which is like any time my three year old tries to show my one year old how to do anything.
Spencer – I tried to track down the Spencer Trappist Brewery (even though they don’t do tours) When I arrived at the dot on the GPS, I found only an abandoned school bus. So, uh, I need another shot at this one. Update: I found it! The abbey, which is very cool, is open to the public, but the rest of the premises are guarded by signs asking you to respect the monastic nature of the place and keep out. As a guy who spends most of his time driving around with two small children, I can appreciate someone just wanting to be left alone.
Stockbridge – Most of our time was spent hiking the Ice Glen – a ravine that receives little sunlight and can hold onto snow into the summer. Fellow Lit Nerds: Melville alluded to it in Moby Dick! We didn’t see any snow, but on an 85 degree August day, I would say it felt close to 50 degrees in some of the low points. You also enter the trail via the rope bridge from Temple of Doom, which was harrowing. Downtown Stockbridge has that cool, throwback New England vibe. I thought my coffee tasted funny, but then I realized they just didn’t use artificial syrups or chemical crap – I don’t care, next time, give me all the syrups.
Stow – Tried to make up for a rained-out round of golf by visiting the driving range at Stow Acres. My biggest takeaway is that I need to keep my head down through my swing.
Sunderland – When a tree claims to be the biggest east of the Mississippi, you get in your car and drive two hours to touch it. I came back later on my own to explore the Sunderland Caves, and I can’t stress how awesome they were, particularly in a state that isn’t rife with caves.
Swansea – Cornerstone is a no-frills Portuguese bakery and diner. I went with the sweet bread French toast. This guy above was hanging out in front of the bank next door, which doesn’t make much more sense than it would’ve in front of the diner.
Tewksbury – Vic’s Waffle House is a bustling old school diner with some creative waffle combinations. There were more intrepid offerings than my Chocolate Pig Waffle (chocolate chips and bacon) but I am not an intrepid eater.
Topsfield – The flip side of this should be recognizable from rte 95, but only recently did I learn that the Alfalfa Farm was actually a winery. Unfortunately, perhaps due to miscommunication, no one was there to receive me during my visit.
Tyngsboro – This space used to talk about the Pheasant Lane Mall, which I have since discovered is over the town line in Nashua, NH, plus, I had spelled “pheasant” wrong. To make amends, I got a $6 frappe from Sullivan Farms, and it was worth every penny.
Uxbridge – I have stopped at Jumbo Donuts downtown for coffee on my way back from the Webster/Douglas area. It’s a solid local cup.
Walpole – As my wife’s hometown, this would be a perfect spot to make fun of the ongoing “controversy” surrounding a giant rock painted like Snoopy wearing a mask or not, but instead, I’ll give a shoutout to Conrad’s, our family’s favorite spot for Friday dinner. Keno at every table!
Wareham – Across from Onset Beach is the Quahog Republic, home of one of the best vibes (and stuffies) of any of the beach front seafood restaurants in the southeastern part of the state.
Washington – When you see “Appalachian Trail”, you think of a 2160-mile, 14-state juggernaut, but I’m here to tell you that if you enter from Blotz Road in Washington, you are facing a footpath designed for squirrels and other small mammals.
Webster – A town in the midst of renewal. We spent the day around Lake Chaubunggungamaug, and found a lake side bar that felt simultaneously like a hidden gem and something that wasn’t maximizing its potential. I bet if I did this in five years, Webster would move up the list the most.
Wendell – Above is Ruggles Pond, the starting point for the hike to Lynn’s Falls in Wendell State Park. Lynn’s Falls were not the most impressive as far as waterfalls goes, but the brook that runs parallel to the trail makes for a pleasant hike.
West Bridgewater – Above is the Solitude Stone, a strange landmark in the Bridgewater Triangle where some 18th century preacher carved a cryptic poem into a rock. It’s also known as the “Suicide Stone” for more tragic reasons, which is a fun thing to have right across the street from a handful of houses in this neighborhood
West Springfield – Did I drive my kids two hours just to get us a donut the size of my head? (It was worth it; thank you Donut Dip.) Later, I circled back and picked up some PTO Pilsner from Two Weeks Notice Brewery for a Bruins game, and I encourage you to do the same. Next time, I’ll need to stay and enjoy their indoor/outdoor set up.
Westboro – In 2002, I met a girl at an accepted students night for Hofstra and the following week, she randomly offered me Celtics playoff tickets that her family wasn’t using (???) That game ended up being Game 3 of the 2002 Eastern Conference Finals aka the biggest comeback in NBA Playoff history. We only hung out a few times in college, but god bless her. If you stop by Rocco’s Donuts, big thumbs up to the muddy buddy.
Westhampton – We picked up lunch from Outlook Farm (more than just a farm to be sure) and lunched at Mineral Hills Winery. Thumbs up to the Happy Hog sandwich (good balance of pulled pork and sauce) but thumbs down to the Mac Dog (mediocre mac and cheese plus a mediocre hot dog do not add up to greater than the sum of their parts.)
Westport – I frequented Horseneck Beach in high school, including spending the entire day there before the first day of hitting drills for football senior year. When I got hit, I curled up in a ball, only slightly worse than my usual output. You see, my body was covered head to toe in sun poisoning. I spent a week smothered in aloe.
Whately – Paid a visit to Tom’s Hot Dog stand. The Bacon Dog is a simple concept – it’s just a strip of thick bacon sandwiched between the dog and the bun, but I don’t know if I ever want to have a hot dog differently afterwards. We won’t talk about my side of mac and cheese.
Williamsburg – Saw the Williamsburg General Store on Chronicle, and couldn’t pass through town without stopping. It rivals Huntington’s General Store in so many ways that I wouldn’t be surprised if they were owned by the same people. The family scarfed a bag of homemade cookies on our ride home. Also got a Williamsburger from the Local Burgy food truck. Anything with brisket, I’m in.
Winchendon – What a strange place “Toy Town” is. We got our picture of Clyde II, the giant rocking horse. There’s a fancy prep school, but one that looks more like a prestigious summer camp, or 70s corporate retreat center. There is an uninspiring walking path right across from two of the more opulent cemeteries. I asked my central mass expert for his thoughts, and he simply told me it was commonly referred to as “Winchentucky” and that he wasn’t allowed back there. Oh.
Winthrop – Like most boys of the 80s, I’ve had the random craving in adulthood for the retro video games of my youth. Sudden Impact, a small storefront full of Nintendo and SNES games among others, gave me that gift.
Worthington – In terms of general stores, Corner Grocery left much to be desired, though to be fair, it’s not a general store in the traditional sense. More alarming was that at one point, I was stuck so deep on a dirt road, surrounded by dilapidated houses that I thought was about to get Deliveranced only to find that when I finally emerged onto the paved road, there was a sign pointing back the way I came as if there was stuff worth seeing back there.
Amesbury – Amesbury has a really cool downtown with many restaurants and shops centered around a resurrected mill and roaring river. Above is the Blue Moon Restaurant.
Aquinnah – This was a regrettably quick stop, as I didn’t want to test the patience of the bus driver who was taking me back to the ferry. So while I got a look at Gay Head Lighthouse and Moshup Beach from a distance, I’d like to come back with my kids to check out the cliffs.
Ashby – Trap Falls was a great find for a parent with young kids. The brook only runs about knee deep, but there is an awesome trio of waterfalls that gives it a unique combination of beauty and a space to play. It’s located just off the road in Willard Brook State Park.
Athol – It’s like Southbridge, but an hour north. Quintessential mill town. Athol also leads the league in bars that you could tell me are currently open or closed twenty years ago, and I’d believe you either way.
Avon – Jordan’s Furniture is a great place to go and not buy furniture. You might practice phrases such as “they had a lot of nice stuff, but nothing I loved”, or “I found one set, but it was like $5000, so no thanks!” We’re like 0 for 4 at this point. Thanks for the memories, Avon.
Barre – We spent a Saturday at the Stone Cow Brewery where we sampled the wears, ate the signature smoked wings, and the boys enjoyed sledding down the hill, even if I almost took out a nine year old on the first run of the day and came to rest mere feet from a creek.
Belchertown – Above is the Caramel Bacon Waffle from Almeida’s Country Cafe. I suggest letting the ice cream melt so it becomes like butter spread on the waffle…I should probably go to the gym.
Berkley – Visited the mysterious Dighton Rock, one corner of the Bridgewater Triangle.
Beverly – We did a short hike at the JC Phillips Reserve up to the ruins of the Phillips Mansion. I later did a personal taste test between rival chicken sandwiches at Flip The Bird and Butter UR Biscuit. I thought Flip the Bird’s Nashville fried chicken sandwich would coast to victory, but that was not the case – Butter UR Biscuit was the superior sammy.
Blandford – Or you could be magically whisked away to…Blandford…Hey… we’re in Blandford.
Bourne – Rotaries are a Massachusetts art form, and here is where I cut my teeth as one of the state’s foremost Rotary Wranglers. I’d also like to pour one out for the Mashnee Island Grill, one of the finest outdoor establishments on the Cape. My sister got married here, too, although that probably shouldn’t have been mentioned last.
Boylston – Tower Hill Botanic Gardens is beautiful and also not the ideal place to bring two kids under the age of four. I left with the older one tucked in my arm like a sleeping bag, screaming because he wanted to climb into the fountain and touch the turtle statue. We brought the median age down to 85.
Bridgewater – On a brisk December afternoon, we visited Stanley Iron Works Park, the site of an old factory on the Taunton river. Some of the old machinery and canal work still exist.
Brookfield – There was a fried seafood restaurant here, but this is about the point inland where I start getting skeptical of the quality of seafood. Instead, I found Spooner’s Well, where some woman threw her murdered husband’s body in the 17th century. Brookfield!
Burlington – There was a time where braving the hordes of the Burlington Mall was the only way for me to get Chick-Fil-a. Progress. I also saw The Purge here, which I’m still deeply disappointed in. You have this original, complex concept, and you hardly explore it. It’s like having a Maserati and only using it to drive the ten feet to the mailbox at the top of the driveway. It’s the only time I’ve wanted a horror movie to be longer.
Carlisle – Carlisle is a town in Massachusetts.
Charlton – Treehouse is what Trillium should be. The Pike rest stop has come in handy a few times as well, although I’m not sure if that counts or not.
Chelsea – Finally made it to Ciao Pizzeria, which regularly appears on lists for top pizza places around the state. While it was good, it’s not making my list. Kind of like gourmet Bertucci’s.
Chesterfield – The Chesterfield Gorge was pretty awe-inspiring, and it looked like further down river, there was a space for tubing and swimming, but I didn’t get a chance to check it out because my three year old was tired and trying to claw my eyes.
Clarksburg – This is the rarely seen Massachusetts switchback on Route 2 in Clarksburg from the parking lot of the Golden Eagle Restaurant.
Colrain – Just realized I’m wearing the same outfit as I am in the Dalton picture next to this, but a month apart. Sounds right. Anyway, I’m not a big leaf peeper, but Colrain was striking and serene, particularly along Green River Road. The yellow leaves made the river look aflame on our way to Stafford Brook Falls.
Cummington – We first stopped at The Old Creamery Co-Op, a small market that works to collectively support local farms and other food producers. I enjoyed both a breakfast sandwich and an exceptionally rich brownie. Then I took the boys to the William Cullen Bryant Homestead, where I recited “Thanatopsis” as they contemplated man’s existence aka Griffen put rocks in his mouth.
Dartmouth – I almost attended UMass-Dartmouth, which reminds me of when I went to visit a friend there in high school, but was too afraid to drive on the highway, so I took route 140 from Franklin all the way using only a book of road maps because no one had cell phones yet. It took twice as long as it should and I arrived to a concerned call from my parents.
Dennis – On New Year’s Eve around 1994, my dad and I saw Cutthroat Island at the Dennis movie theater and I couldn’t believe we were the only two people there. Having seen parts of Cutthroat Island since, I’m no longer surprised.
Dover – I grew up ten minutes from Dover and just found out three months ago there is supposedly a demon in the woods there. I’m bummed; high school me would’ve been all over tracking it down. Other than that, Dover makes me think of the rumor that disgraced former Celtics coach Rick Pitino supposedly lived there among the farmhouse mansions, though I can’t say why we all thought that.
Dunstable – The Farmhouse Cafe may or may not be the only restaurant in town, but that’s okay, because the chocolate chip Belgian waffle was the bomb.
East Brookfield – Timberyard Brewery, located right on the Spencer town line, has a cool, rustic indoor space, a patio, then a back picnic table area. Not only did each table offer a heat lamp, but they had fire pits you could drag to your table which they would continually stock and stoke during your visit as well. Very hospitable, and a solid Belgian wit, too.
Easthampton – To appropriate Thoreau, we sucked the damn marrow out of Easthampton. I started with a cheesy garlic bagel from Tandem Bagel (excellent), then took the boys to the playground in Nonotuck Park (top marks for the treehouse and backdrop of Mt. Tom). We then took a walk on the Manhan Rail Trail, which allowed me to easily swing the stroller by Abandoned Building and New City Breweries (keep your judgments to yourself) and grab lunch from Riff’s Joint (BBQ pulled chicken egg rolls were great, Bulgogi cheesesteak not so much). We ended with some of the best ice cream I’ve ever had from Mt. Tom’s Homemade Ice Cream. It was a remarkable combination of smoothness and density. That we ran out of time and I didn’t get a chance to explore Mill 180 among other things speaks to how much Easthampton has going on for such a small town.
Egremont – For such a small town, French Park was well-maintained and offered a lot of amenities;, including a horse paddock. As the parent of a child enduring potty training, I also appreciated the decency of the public bathrooms.
Everett – I’ve scouted some football games, and after one game, my buddy and I went to Stewart’s and I took over the jukebox. Shortly thereafter, a bachelorette party came in an I wasn’t sure how’d they like my taste in music, but I got A LOT of props for “Let’s Hear it For the Boy” off the Footloose soundtrack.
Falmouth – I’ve attended a couple Falmouth Road Races, visited friends, and visited a former professor here. If I had my choice of anywhere to live on the cape, it’d probably be Falmouth. Above is the Quahog Republic Dive Bar in East Falmouth.
Foxboro – The Pats and Patriot Place are obvious. I watched the final Game of Thrones episode at the Rodman Performing Arts Center. You rent out a theater for you and your friends for only $200. It was a great deal, minus what happened on screen.
Freetown – I once spent an hour driving around the Freetown-Fall River State Forest trying to find the haunted ledge with my kids in tow because COVID makes you desperate for activities outside of the house. I feel slightly better because Google Maps labels the ledge “Good for Kids”. (I’m not sure I agree). After returning later for a solo trip, I found the ledge much more graffitied than scary. Hard to be spooked when someone spray painted the word “balls” beneath your feet.
Gill – The Wagon Wheel is a perfect lunch stop on the way out west along Route 2. A lot of places will try to do too much with a Cowboy burger, but not here.
Gosnold – We visited the smallest town in Massachusetts in April, when the population is somewhere between its December low of 10 and summer peak of 400. There’s lots of bizarre little nuggets about this place to us mainlanders, but my favorite was stumbling across a patch of grass labeled an “active runway” crossing that asked you to look both ways for oncoming planes. Above, we’re standing on one of the shipwrecks that reinforces Barges Beach.
Granville – The Granville General Store is another solid western mass general store, though not as big as some. I particularly enjoyed the pot belly stove, local food for sale behind the counter, and list of every previous owner over 170 years above the entrance.
Groton – Groton is one of the most beautiful towns I’ve seen, right up there with Cohasset, but in a very different way. It looks like the idyllic colonial town with an infusion of modern money. The prep school campuses are out of a movie, and the nature trails are serene. I regret not having stopped at the Gibbet Hill Grill on our way down from Bancroft’s Castle.
Halifax – On the main road, there’s a sign that says “Famous Legs Monument” with an arrow pointing into a neighborhood. Naturally, I checked it out. Then you get there, and it’s…a seven-foot-tall pair of stone legs. Myles Standish’s legs, to be exact, the commander of the Mayflower. On a platform of rail ties in front of an American flag truck. With no indication as to the whereabouts of his other parts. Okay, Halifax.
Hancock – Shaped like a lower case “L”, Hancock has two notable landmarks – the Shaker Village (above) in the south, and Jiminy Peak ski mountain in the north, and there is no road connecting the north to the south. At under 1000 residents, they should just give half to Williamstown and half to Richmond and be done with it.
Hardwick – My children delighted in the covered bridge, my wife and I failed on another test of the random scratchy corollary, and we enjoyed the scenes of Hardwick Winery. Apologies to the two older women on bikes who I gave wrong directions to rather than admit that I wasn’t from there.
Hatfield – Broke even on our test of the Random Scratchy Corollary at the Hatfield Market. Not that I’m a mill aficionado, but I have to say I was disappointed in the Old Mill Historic District – I only saw one mill, and you couldn’t even get a good view of it. There were, however, a couple random pubs I could’ve seen myself stopping in at, but, you know, kids.
Heath – This is as close as you can get to the Burnt Hill Stone Circle, a ring of Stonehenge-ish like rocks of unknown origin that was said to inspire a story by H.P. Lovecraft because it is on private property. Cool, dude – way to hog the monoliths.
Holbrook – We picked up lunch from The Brook. Thumbs up for the mango habanero dry rub on the chicken in the Brook Platter. This looks like another place to be added to a long list of places that would be fun to come back to without kids, but that’s probably the next 15 years of my life.
Holliston – Ah, home. Let me help you maximize your time in town. Get breakfast at Coffee Haven, take a stroll on the rail trail, buy something you don’t really need at Fiske’s, get a sandwich from Superette or Corner Market for lunch, hang out in front of Mobil because there’s nothing else to do, explore the Antique District, just kidding, but really, why are there like four antique stores all within two blocks of each other, dinner at Casey’s, I suggest the wings and the pulled pork. If you want pizza, anyone telling you Table Top is misguided – you want the buffalo chicken calzone from Bazel’s. Also of note: you can enjoy Stoddard Park, but don’t swim in Lake WInthrop, the best neighborhood to trick or treat in is Queens, and not one person who grew up in town actually cares about Balancing Rock.
Hopkinton – Cornell’s is as good of a small town watering hole as any. There’s also a great state park here with a series of trails, man-made dams, and spillways creating leveled reservoirs around scattered picnic areas.
Hull – Took the boys to Fort Revere Park, which is home to a fantastic view AND a series of graffiti-ed tunnels that smell like urine. The best of both worlds?
Kingston – I’ve been to a pair of weddings at Indian Pond, and while it’s a beautiful setting, what’s up with the house randomly perched in the middle of the golf course overlooking the outdoor venue? Can anyone live there?
Lanesboro – For a small town in the Berkshires, we had a surprisingly hard time sorting through our dining options. Ultimately, we went with the Brookhouse for its giant back lawn on a pond, In subsequent trips, I’ve tried the Old Forge (awesome atmosphere, but the Buff Orpington wings were disappointing) and the Lakeside Bar and Grille (nice view of Lake Pontoosac; the only time my kid sat still was when I let him “fill out” his own Keno ticket.)
Leicester – First off, I consider myself an expert MA town pronouncer (Haverhill, Peabody, Dedham, etc) but I have to admit I didn’t start calling this place “Lester” until a couple years ago. I took a stroll in the woods to the Spider Gates Cemetery, one of the state’s preeminent haunted locales, and what did I find? Two people dressed in all black, kneeling on “The Alter”, the site of supposed Satanic sacrificial rituals. Then one waved and lit up a cig. Anti-climactic horror movie scene. Still happy I didn’t have the boys with me. Also, no, I did not pass through the main gates that are supposedly a portal to hell because 2020.
Leverett – We took a hike up Rattlesnake Gutter, which feels like a misnomer. It’s more than a gutter, but less than a canyon. Not quite a ravine, but more than a trench. Let’s go with gulch. Starting level, the trail ascends roughly 100-200 feet above the gulch as they run parallel to one another. At the higher spots, there are places to cross over and check out some serious rock faces. Above is Keegan running away from me on yet another trail that neither of us have ever been on. We also stopped by the Peace Pagoda.
Lincoln – The DeCordova museum is a really cool area to bring your kids, specifically the sculpture garden. On your visit to Lincoln, you may be tempted to visit “Ponyhenge”, a local oddity involving rocking horses in a pasture, but I am here to assure you it is merely a mysterious pile of garbage. I don’t get the allure.
Lowell – Their tournament is the premiere in-season wrestling event all winter, and a visit to the Lowell Beer Works before the finals had been a tradition, but it looks like it’s now a taco bar.
Lynn – If you look up “High Rock Tower” on Wikipedia, all it mentions was the Hutchinson Family Singers once owned it before selling it to the city. What it doesn’t tell you is they once let spiritualist John Murray Spear build his “God Machine” there, a mechanical being meant to be imbued with supernatural powers that would become our new messiah. (Update: it did not.)
Manchester-by-the-Sea – Ugh, just cut the last three words off already. In a state where about 70 towns have direct access to the ocean, you might as well be “Manchester-with-the-Trees”. Anyway, the boys and I hiked Agassiz Rock, which was cool except for being scared my kids would get wedged under the massive boulder and I wouldn’t be able to get them out. You know, normal parenting fears.
Marion – Wareham, but fancy. Ideally, I’d like to visit the Brew Fish’s patio with my wife and no kids in the summer, but I wound up here in February, so I picked up a cup of coffee from Uncle Jon’s instead.
Mashpee – I’m not sure how much this one counts, not because I haven’t been to Mashpee, but because it was visiting a friend at New Seabury. It’s a part of Mashpee, but has it’s own census-designation, and mostly consists of rich summer homes. On Google Maps, “NEW SEABURY” is so big it makes it look like a state in which Mashpee resides.
Medfield – The non-locals might know Medfield State Hospital from appearing in the movie Shutter Island, but we know it better as the site of the best sledding hill in the area. Knives Out also shot a scene at the bottom of this street.
Melrose – A short hike in the Middlesex Fells led me to the cascade that serves as the only natural waterfall in the Boston area. Careful if you have little ones: the trail is short, but the stairs that take you from the top of the falls to the view below are a bear.
Methuen – At the top of Greycourt State Park is the ruins of a castle that overlooks Methuen City Hall. Unrelated: In college, I was at a party once and someone was like, “Oh, aren’t you from Boston?” and I said “No, I’m outside of the city.” They said, “Well, these guys are from Boston.” So I asked them what part, and in a strong Merrimack Valley accent, they said, “Methuen.” Which borders New Hampshire. Not Boston. And now I unfairly think most people from Methuen do this.
Middleton – The wife and I got a filling meal at Maggie’s Farm, and I regret that we weren’t able to sit inside, because the vibe was great. We also bought the boys ice cream across the street at Richardson’s. I know this makes two posts about Coffee Oreo ice cream, but Coffee Oreo ice cream is the best thing to come out of 2020.
Millis – I’m not sure who said “we need a NASCAR themed bar in a random Massachusetts suburb”, or what their reasoning was, but I’m glad they did. Toscanini Farm also has a Hay Maze that one experienced three year old would describe as “terrifying.”
Monroe – Did someone say “hydroelectric dams”!? No? Oh, well Monroe’s got them for you anyway.
Monterey – The brisket sandwich at the Roadside Cafe was awesome. You also wouldn’t think that a small restaurant out in the middle of nowhere would have the most strict Covid protocols, but they weren’t screwing around.
Nahant – It says “Northeastern Marine Science Center” but if that’s not a Bond villain’s underground lair, then I don’t know what is.
Needham – Some of the greatest slow pitch softball games ever played happened here with my summer camp coworkers in 2002. I remember more about those games – the lineups, the bloopers, the stakes – than I do about most of my own birthdays.
New Braintree – Took a stroll down the Mass Central Rail Trail. These are the signs you see in Central Mass that you don’t see back East.
Newbury – The house above is an illustration of pettiness, and it’s pretty great. In the 1920s, the terms of a divorce settlement demanded that the ex-husband build a house for his now ex-wife. It did not give any other details, however, so he chose the worst possible location in the middle of the Plum Island marshes and painted it a hideous shade of pink. Even the plumbing used salt water, making the house worthless. Later, John Mellancamp would write a song about it.
Norfolk – Head to the Eaglebrook Saloon for the best bar pizza and homemade blueberry beer in the region.
North Attleboro – Holy maple bacon dipping sauce. KC’s Burger Bar is outstanding. Try a shake with your meal. Meanwhile, World War I Park above has a petting zoo and a super long slide.
Northampton – Very cool, if a little bit crunchy, town. Many towns have bike paths, but Northampton has a whole network, complete with intersections and all. Picked up a dynamite cup of mocha coffee from Le Familiars, a coffee shop in an old diner car downtown.
Northfield – A delightful little hamlet with an air of spiritualism. There are a number of different churches, St. Thomas Aquinas College, and it once housed members of the Brotherhood of the Spirit Commune, and so on. I even passed one house with a giant pentagram over the garage. Though I can’t say I know what’s going on above. Stopped for ice cream for the boys and wine for the wife. The people couldn’t have been nicer.
Norwood – Lewis’s is one of our favorite local destinations these days for casual dinner and drinks, and Jam Time is money well-spent if you don’t mind the chaos that is one hundred screaming children.
Orange – The Boiler Bar and Grill is a hidden gem tucked out of the way on the shores of Tully Pond. The repurposed mill has a trendy bar side with charging stations that rise right out of the bar top, and the dining room’s high-backed benches provided privacy and made it impossible for my kids to torment our neighbors.
Oxford – Huguenots and Clara Barton, that’s what Oxford does! If French Calvinists aren’t enough for ya, N & J Donuts offers a variety of fresh homemade donuts, among them the only triple chocolate donut on (this) record. The wife doesn’t do chocolate, but spoke highly of this one, so that’s saying something.
Peabody – I went to a wedding at Brooksby Farm and had my first Sonic experience up here. Long live Texas Toast buns.
Pepperell – Came for the covered bridge, stayed for the Breen’s Diner chicken and waffles, which would’ve made Guy Fieri weep tears of joy.
Phillipston – The Red Apple Farm is fantastic. Not too crowded, good food, sweet brewery, live music, and so on. A great way to spend Father’s Day.
Plymouth – Plymouth is a great weekend getaway regardless of how disappointing the rock is. My favorite thing so far are the inhuman stuffed pretzels at the Driftwood. On my to do list, however, is Brown’s Bank in the summer. All I need is a friend with a boat. Update: Apparently the Driftwood is gone, which is a travesty, so instead there’s the Hotel 1620 where we’ve stayed for a couple weddings.
Provincetown – The journey up to P-Town wearing the boys out put the kibosh on ascending the Pilgrim Monument, so we settled for lunch from a hot dog stand in a very crowded Lopes Square. It’s probably for the best we didn’t trap ourselves in a small tower with strangers since the above picture ended up being taken mid-Delta cluster.
Raynham – The pu pu platter from 2 Jerks BBQ contained some of the thickest spare ribs and bacon I’ve ever had, but the highlight might’ve been the dry rub smoked wings. Next door is a giant milk bottle.
Revere – I had a blast at a hip hop show at Sammy’s Patio in Revere Beach.
Rockland – I have stayed at the Double Tree a couple times for wrestling tournaments. I will readily admit this entry badly needs an update.
Rowley – My sister had her first apartment up here. She took me down the road to the Agawam Diner in the days before I really appreciated a good diner.
Rutland – Ever tell your kid that they’re the “center of your world”? Well, I did you one better – I took my kids to the geographic center of Massachusetts! Seriously, they fenced off a tree on someone’s lawn and everything. We also stopped at Schultz’s Farm, where my kids enjoyed feeding the animals, and I enjoyed feeding myself some mac n’ cheese that was next level.
Sandisfield – The Hammertown Loop in the Clam River Reserve is a clearly marked, peaceful trail in an old growth forest.
Savoy – Forget Bash Bish – Tannery are the best falls in the state. We were lucky to catch them after four days of melting snow so they were at full force. The litany of smaller unnamed falls and the also impressive Park Brook Falls around the corner are all cherries on top. Worth driving deep into nowhere.
Sharon – Fun story: I went to a wedding here with a recently minted ex-girlfriend, and who was there? My future wife, though I didn’t know it at the time, and have spent the years in between swearing that I noticed her as one of the bridesmaids. The above picture was taken at Ward’s Berry Farm.
Sherborn – C&L Frosty was an important ice cream shop to me growing up, and Rocky Narrows is a cool place for a hike along the Charles.
Shutesbury – I paid a visit to Shutesbury’s infamously small library (supposedly so small that it has no running water) and was disappointed to find that while it was small, it wasn’t gnome small.
South Hadley – Picked up a book from Odyssey Bookstore, and a coffee from the small market next door that caters to Mount Holyoke students. Then, on our way out, I picked up some pilsners from Drunken Rabbit Brewery.
Southbridge – You thought I didn’t know about “The Eye of the Commonwealth”?! There’s an aura of another tired mill town at risk of being left behind, but I have to feel the old American Optics factory that looms over the center of town can be converted towards more contemporary use like a number of other factory towns in the state.
Springfield – Theodore’s Blues, Booze, and Barbecue is one of western mass’s preeminent BBQ joints. The burnt ends in particular were excellent.
Stoneham – We ventured into the Virginia Wood to look for the lost mill town of Haywardville. I don’t think we found most of it – unfortunately, steep trails and slippery leaves are a tough combination for a one year old and cut the hike short.
Sturbridge – We hiked through Tantiusques, which was doable for the kids, and cool to see an old graphite mine, although we could only get so close due to standing water.
Sutton – For my money, the coolest natural feature in Massachusetts resides in Sutton – Purgatory Chasm. The trail is short, but with so much to explore in both the chasm and along its sides, it’s worth an entire afternoon. Addendum: Is this a good place to bring two small kids by yourself? Absolutely not. Ended up carrying sixty pounds straight uphill the entire second half.
Taunton – Kinfolk is touted as one of the best BBQ restaurants in the state, and I’d go back a second time. The ribs were the best part of the meal and the best I’ve had in years.
Tisbury – Perhaps better known as Vineyard Haven. The author William Styron is buried in West Chop Cemetery. Styron is most acclaimed for Sophie’s Choice and The Confessions of Nat Turner, but was more recently remembered for his essay “Darkness Visible,” which was one of the first visible pieces of non-fiction from an author regarding their mental health and depression. Having read about his bout with near-lethal depression makes his epitaph hit a little harder; It’s a quote from the end of Dante’s Inferno where the speaker emerges from hell to behold a peaceful evening sky.
Townsend – Townsend is a very cool little New England town. I could spend hours on the patio at Cliff’s Cafe. It looks like stuff goes down at Yee’s Village. And North Middlesex is another one of those contemporary regional high schools no one knows about but has a really cool modern design.
Tyringham – Worth the drive. Ashintully Gardens is a singular scene of scenic joy, particularly “The Marble Palace” at the top of the hill. If you want to see inside of Santarella, (The Gingerbread House of Tyringham) plan ahead and arrange a visit – you can’t just show up.
Wakefield – We’ve attended the 4th of July parade here twice as a family, and both times there was a moment where we were having a good time and I realized every other young kid but mine were wearing headphones for the noise. Gotta love those “Crap, should I be doing that too?” parenting moments.
Waltham – I lived in Waltham for three years, and I loved it. Moody Street is underrated, with Shoppers being my favorite spot. Also, even though I quickly learned that I was not “local” enough for Michael Jay’s, I miss it anyway.
Warren – Another Central Mass mill town along the Quaboag River, we tested the RSC at the Village Market, a local general store with a cozy interior.
Watertown – Once, I was at the Halfway Cafe with one of my good friends and he was telling me about how he was going to meet up with this girl even though he moving back to Vermont the next day. I told him it was a bad idea; he was wasting his time. Welp, they’ve been married for three years now, and I was in the wedding. So, I’m an idiot.
Wellesley – I could choose to unload my complex history with the town of Wellesley, which was home to both my first school and first summer job, but instead, I’ll just say Linden Store is the bomb – best meatball sub in the state!
Wenham – The boys tried their first peppermint patties from Winfrey’s, a small candy shop chain on the North Shore.
West Brookfield – I am a cool dad because I took my kids to a) an independent bookstore to look at antique books or b) the grave of Dietrich Leetouwer, the man credited with introducing asparagus to the New World. (We also went to the Rock House Reservation, an awesome short hike involving caves built into large rock outcroppings.)
West Stockbridge – The Shaker Mill Book Store appeals to every level of bibliophile. From the racks outside that have surprisingly familiar and respected titles on sale for 12 for $10, to the expensive collection of rare and first editions behind the counter inside, I could’ve dorked out here for hours. There were a few more places I wanted to see, specifically the Turn Park Sculpture Garden, but time tends to run short when you’re on the edge of the world.
Westfield – I took a stroll through Stanley Park, stopping to do some reading by a working mill wheel and get stalked by overly-comfortable geese.
Westminster – Spent a number of nights skiing at Wachusett in high school. More recently, I stopped by the Wachusett Brewery, which has a great outdoor seating area to relax and have a blueberry ale.
Westwood – For a town that was a theoretical sports rival and home of my cousins, I have surprisingly little to say about Westwood. One time, my buddy made my future wife cook his kids pancakes here. That’s about it.
Whitman – I don’t care if the above sign and plaque are a random eyesore in a parking lot between a Wendy’s and a Walgreens – they invented the gad dang chocolate chip cookie, yo! As in Toll House cookies! They need to capitalize on this more as a community. If anyone wants to petition the local high school to change it’s mascot to the Tollies, let me be the first to sign up.
Williamstown – Located on the edge of the Williams College campus, Hot Tomatoes serves delicious Neapolitan pizza on a serene patio overlooking a river.
Winchester – I knew Winchester was nice, but I was surprised at just how upscale it was. Reminded me of a more densely populated Wellesley. Book Ends was a well-kept local bookstore with a wide selection for a limited space.
Woburn – I underestimated Woburn. I blame the movie, “A Civil Action.” Downtown has a chic array of bars and restaurants, but I chose to get some authentic Chinese food from Gene’s Chinese Flatbreads. They advertise that they specialize in food from “western China” which I guess is a rarity, but based on how good the pork flatbreads in particular were, I don’t know why everyone wouldn’t add them to their menu.
Wrentham – Hey! I live here! My only gripe is that the dirtbikers that occupy the state forest every weekend have destroyed the hiking trails to the point that many are impassable mud. They are the suburbs version of those insufferable cyclists that bomb around Cambridge under the laughable delusion they are equal to a car. Actually, that’s not a great analogy, but the moral is bikes of all forms stink.
Amherst – The Hanger has perhaps the best boneless wings in the state. Antonio’s has perhaps the best pizza. When we were in high school, we visited my buddy’s sister out here and she took us to a party. We tried to play it cool by saying we were in college already, until one friend panicked and spilled the beans at the first sign of pressure.
Arlington – It turns out not only was Uncle Sam a real person, but he was born right here in Arlington, and there’s a statue dedicated to him on the bike trail. I want YOU to avoid making any lame jokes in this section (I despise myself right now.)
Ashfield – The family spent the day at Chapel Brook Falls. The kids required a little bit more supervision than at Umpachene in New Marlboro, and the water was colder, but it paid off with a natural waterslide at the bottom of three separate tiers of swimming areas. I expect we’ll go back at some point, as it will only get more fun there as the boys get older.
Attleboro – I picked up my wife from the MBTA station here once on our way to getting swindled on a car with a bad transmission. Feels strangely urban compared to its neighboring towns until you realize that Pawtucket and Providence are right on the other side. Which brings me to my next point – never do business at Diamond Auto Sales in Cumberland.
Ayer – Pirone Park has one of those great labyrinthine wooden playgrounds from the 90s complete with bridges, tunnels, tire pit, and plenty of tight places for an unwitting parent to get stuck.
Becket – Between the abandoned machinery and trees encased in ice, the Land Trust Quarry was surreal the day after a storm. The part that made me anxious, however, was all those fresh foot prints across the ice below.
Bellingham – Every boy remembers the town where he had his first Bloomin’ Onion at an Outback Steakhouse…anyway, I once got lunch by myself at the 140 Pub n’ Club, and for some reason, some people find that funny, like it’s not a thing one does. But the food was fine, and I enjoyed myself, so the haters can kick rocks. Urban Air is an indoor play place that makes Chuck E. Cheese look like the RMV.
Berlin – My great aunt and uncle lived here when I was growing up. I vaguely remember their funeral in town. So, uh, yeah…do with that what you will.
Billerica – I got a sub at the Turnpike Market, an upscale grocery/deli. The combo of steak and bacon was intriguing, but Sweet Baby Ray’s was too sweet as far as a sauce. The pizza looked like the choice for a return visit.
Bolton – My dad worked in Bolton, but more recently, I’ve been to the Nashoba Valley Winery. It’s a fine place, and I’d go back, but I’m happy to say because of my choice in spouse, I will never have to go apple picking there or anywhere else. This is what we call “marrying well.”
Boxboro – Pony Shack Cidery is a small, independent cider house that deals in a wide variety of beverages, including the above Russian Donkey, which is a Moscow Mule crossed with an apple cider. The guy was really friendly, flexible, and offers tastings on demand.
Braintree – Neither a brain nor a tree: discuss. One of my favorite early dates with my wife was when we both had snow days and trekked through two foot drifts to take the T one stop south so we could walk a block and spend all day at Chili’s. Braintree is also home to the strangest Mary Lou’s in the state,; it looks like someone renovated their living room to open a coffee shop out of their house.
Brimfield – This picture sums up my feelings about Brimfield. We tried to go to Brimfield Tower at Steerage Rock, but the only trail we could find was blocked and had private property signs all over it, so all Brimfield had to offer was a bunch of empty fairgrounds and antique stores.
Brookline – I once did a reading at the Brookline Booksmith which featured a risque story about dating Taylor Swift and sock puppets while my mom and sister were in the front row. The experience was Kafkaesque, minus the bugs.
Cambridge – As a former Central Square resident, I can confidently say that Cambridge is the worst. I still have night terrors of rude cyclists with unwashed hair. So I’ll shift to the time we did trivia with another couple way up at Joe’s Sent Me. It was the final question, and we were in the running for the win. It was a history question, and my friend, a history buff, pounded the table jubilantly and shouted, “Yes! The Trail of Tears!” We won the game, but may have lost the war of perception with our neighboring tables.
Carver – Well, I wanted to take my kids to Edaville, but it mysteriously still had no opening date for 2021 as of the 4th of July. I could’ve done King Richard’s Faire, but I didn’t feel like waiting until the fall just for jousting and mutton. Then I was going to visit MP Sports Cards, but of course the day I was headed there was during their one week vacation. I had to settle for driving down America’s first split highway in the Savery Historic District. Yippee. Maybe I’ll come back, but until then, here’s some friggin’ cranberries.
Chatham – Whatever your opinion of Chatham is, I’m not going to change it here. But I ride for The Squire and the Candy Manor, and I’m bummed they got rid of probably the best wooden playground in history for a more contemporary one.
Cheshire – Well, the Bass Water Grille wasn’t open the day we went, and we didn’t have time for the Ashuwillticook Rail Trail, so we settled for…this cheese press. You see, when Thomas Jefferson became president, Cheshire commemorated the occasion with a 1235 lbs wheel of cheese that they delivered to the White House via sleigh, boat, and horse-drawn wagon. Ultimately, I wish Bass Water Grille had been open.
Chicopee – Good German beer gardens are near impossible to find in Massachusetts. Munich Haus feels randomly dropped into the middle of the city, but if I lived in the area, it would be a go-to spot for an afternoon beer. The above pic was taken immediately after opening, hence the empty seats.
Clinton – Interesting little mill town. There’s a Museum of Russian Icons for all you Fievel Mousekowitz enthusiasts. There’s also an abandoned train tunnel that’s supposed to be haunted. Oh, and if the Wachusett Dam ever bursts, Clinton is toast.
Concord – I’ve been able to partake in a couple of birthday parties at the Musketaquid Sportsman’s Club, and what a magical place. Any lakefront lodge that allows grown men to play around with their homemade potato cannon is all right by me.
Dalton – Wahconah Falls is everything you want with small kids – minimal walk to the falls, lots of rocks to climb on, and a legitimately majestic hunk of nature. Swimming isn’t allowed despite the seemingly deep pool at the foot of the falls, but that would’ve been above our pay grade at this point anyway. I had a hard time peeling my kids away.
Dedham – There’s a lot of places here I like to grab a bite – Brickhouse, Halfway Cafe, Victory – but what’s coming to mind first is when I was at a rehearsal dinner at Moseley’s and wandered upstairs to find a singles dance for senior citizens. Straight out of Cocoon. Very unnerving.
Dighton – You can be forgiven for missing Sweet Knoll State Park, as it appears it’s located in someone’s backyard and the trails are narrow and muddy. Founded only in 2009, it’s possible it is still under development. The rail bridge over the Taunton River is cool, although if you’re crossing it, I suggest walking along the rails themselves, as many of the ties have rotted through.
Dracut – What do you call a town of 30,000 people with upwards of 19 local pizza joints, not including chains or sit-down restaurants that serve pizza? The Unofficial Pizza Capitol of Massachusetts (TM). I did my own Portnoy-esque four slice taste test of some of the highest rated places, and in the end, I give the edge to Brickhouse. Romano’s, Brother’s, and J&J’s all scored high as well, though.
Duxbury – In the background is the Powder Point Bridge, a super long wooden bridge that carries cars out to Duxbury Beach.
East Longmeadow – Took the boys on a stroll along the Redstone Trailway. Pictured above: the old Milton Bradley factory. I also got an Iced Mocha Latte at Shelburne Falls Coffee Roasters because I am a basic bro. It was scrumtrulescent.
Easton – North Easton is one of most beautiful areas around. The town is shovel crazy, including naming their high school after the guy who invented a certain kind of shovel, Oliver Ames. We spent Mother’s Day at the Governor Ames Estate once; just delightful.
Erving – The Farley Ledges is probably one of the most challenging yet rewarding hikes I’ve been on. One could scramble up the cliffs and around in just over an hour, but between the caves, waterfall, and overlook, you could spend most of the day here as well.
Fairhaven – First, Fairhaven High School is so lavish that it reminds me of the high school from 10 Things I Hate About You. In fact, Letters to Cleo might be trapped on the roof of FHS right now. Furthermore, Fort Phoenix Park has a lot of ways to entertain the little ones – the remnants of a Civil War fort, cannons, a rocky ocean beach, boulders to climb on, and a view of a lighthouse and a drawbridge.
Fitchburg – The West Fitchburg Steamline Trail is a cool concept – a recreational trail that follows the piping from the a defunct factory along the river. However, it still needed a little more upkeep, including addressing some evidence of vagrancy.
Framingham – When you grow up in a town like Holliston, you have to go to places like Framingham to find anything to do. Junior and Senior year, Mr. Billiards was a common weekend spot. Afterwards, we’d sometimes go to the Pizza Hut down the road, until the time the host sat in the booth with us and told us he (and the rest of the kitchen) was on acid…that Pizza Hut is no longer there.
Gardner – The world’s biggest chair. We saw it, and it is what it sounds like. The world’s biggest chair. We were back in the car in about 5 minutes.
Gloucester – Went to a couple lovely weddings here, but today, I’m here to speak with you about Dogtown Commons. Do you like abandoned villages with legends of witchcraft? Feral animals? Three dozen boulders strewn about the woods with creepy “motivational” sayings carved into them? Then you belong… in Dogtown Commons.
Grafton – We drove here to get out of the house and randomly buy scratch tickets. You see, my wife has a theory that the more obscure a place you buy your scratch tickets, the more likely you are to win. “No one ever wins at a Mobil in Brookline.” Grafton qualifies as far out enough for us, but I don’t remember winning anything significant.
Great Barrington – I was excited to check out Great Barrington; I left with mixed feelings. On the plus side, I had a solid lunch at the Barrington Brewery, downtown was vibrant and beautiful, and we visited the birthplace of W.E.B. DuBois, who my three-year-old labeled “one of the most important voices of the early 20th century.” (Just kidding; he asked for “five ice creams and three snacks.”) The downside was that only about a quarter of the River Walk was accessible by stroller, and when I looked at it through the lens of “would my wife and I enjoy a weekend away here?” it felt a little too fancy for our taste. Definitely more of a “bistro town” than a “pub town.” We also passed through part of Bard College – if you want to go to school at the commune from Midsommar, then this is the place for you. Don’t forget your bear costume.
Groveland – I’m not sure why Ultimate Perk has five central air units along the drive thru, but it was a very good iced coffee, so who am I to question what they do?
Hamilton – The story of Hamilton is the story of a failed coffee run. I liked the look of Henderson’s Cafe, but it closed twenty minutes before I got there. Then I looked for a place called the Honeycomb, but couldn’t see it from the street. Then the map showed the “Asbury Grove Coffee Shop”, but when I arrived, I found an enclosed faith community that is probably a benevolent place of healing and peace, but because I am an American and afraid of all things I don’t immediately understand, I said “this looks like a cult” and went home empty handed.
Hanover – My sister lives here and loves it. She will probably be mayor by 2025.
Harvard – I was denied in my attempt to visit the Harvard General Store, which looked ominously like a COVID victim, despite their website looking very much updated and active. Hopefully it was more of a closed-over-Thanksgiving-Weekend thing.
Haverhill – We ran the Warrior Dash here, which is like the junior version of a Tough Mudder when those things came in vogue. We each decided to dress up. I wore a wrestling singlet because besides being uncomfortable for everyone else to look at, it’s incredibly lightweight and easy to move in. My friend Rob, meanwhile, chose to be a utility worker – jorts, work boots, hard hat, goggles. It ended poorly. I also got a scar on my hand from where another friend, Dan, stomped my wrist into a rock. Then we all got welts from insects hidden in the mud!
Hingham – We joined our family friends for a hike around World’s End, but due to a lack of effective communication, ended up with an extended picnic and a short hike, so we didn’t quite reach the end. All in all, it was still a breautiful place.
Holden – Lovellville Falls is very cool, but hidden down a dirt road that you’re not really supposed to drive down. Fortunately, it’s an easy walk from the top of Mill Street. I also got a delicious chocolate frappe around the corner at Goodhile’s.
Holyoke – We checked out the Dinosaur Footprints off of Route 5, which held the boys’ attention longer than I thought they would, then we ascended Mt. Tom by car to climb Bray’s Tower and get a bird’s eye view of Easthampton. I don’t advise carrying two small kids up those tower stairs to anyone..
Hubbardston – I know I’m the only person under 40 who has seen Night Shift, but let’s break this down Billy Blazejowski style: Okay, first, Hub, as in the center, like the hub of nothing. Next, you have Bard, as in someone who sings songs, like the bard who sings to trees because no one else is around. And last, you have Ston, as in you’ll be stunned how little there is to do here. Hubbardston. Also, accuse me of having an overactive imagination if you want, but The Country Hen looks like a front for some Machiavellian moves in the Hubbardston underbelly. At the very least they have a grip on this town like Brad Wesley from Roadhouse. Sorry, I’m rambling. Unrelated: We found a beach on Comet Pond for the boys to play around at for a bit.
Huntington – The Huntington Country Store is my new jam. Probably the best local general store I’ve come across in my travels west, and I’ve now been there multiple times as it’s a convenient swing spot from many of those isolated western towns towards the Pike.
Lakeville – In the fall of 1996, I was playing my first season of Pop Warner football, and when I tell you it was ugly, it’s a gross understatement. But the highlight came at Apponequet Regional in Lakeville, where their quarterback wafted a prayer of a throw in the air mid-sack and it landed right in my hands. When I expressed excitement, my coach said, “I’m happy for you, but you were twenty yards away from your assignment.” Better to be lucky than good? In honor of this moment, I give you this picture of Assawompset Pond as a metaphor for my football career as a whole.
Lawrence – Something on Essex Street smelled pretty damn good. The heart of Lawrence’s commercial district is lined with stores and restaurants. I got a coffee from El Taller, an eclectic coffee shop that promotes all things written, and a platter of quipes from Terra Luna, a spacious and welcoming Latin restaurant where I could see myself hanging out all day.
Lenox – The high school mascot is “the Millionaires,” which is, as the kids say, a “mood.” I imagine the name is derived from mansions like Ventfort Hall (above) and Edith Wharton’s house. I had a beer and a pretzel at the Old Heritage Tavern, which was populated by fellow hundred-aires.
Lexington – I was at the driving range in Lexington when the Marathon Bombing happened. An off-duty cop was swinging next to Rob and I, got a call, and we heard his side of the conversation before he ran off and we were left knowing something terrible had just happened.
Littleton – Castle in the Trees is one of the coolest playgrounds in the area, complete with draw bridge, vertical cargo net, and dungeon.
Ludlow – Casa Pizzeria is like the speakeasy of Mass pizza joints. First off, the take out counter looks like it’s in the back of an actual “casa”, so it’s easy to miss. Second, since it’s a side hustle for them, they’re open limited hours and take two months off in the summer. BUT the payoff is worth it – ten styles to pick from, all done from scratch. Imagine having Santarpio’s, Volo’s, and Pizzeria Regina in the same place. Above is a New Haven and a Montanara (deep fried crust.)
Lynnfield – Squished in the woods between Rte 1 Kelly Nissan and a new housing development, you’ll find Skull Cliff, a public art installation created by a guy named Ichabod in 2001. There used to be an inscription that stated the purpose of the work to remind us about how life is fleeting, but has since been covered by lame graffiti as the art that’s still visible slowly fades in the sun. Irony! The message was also particularly grim and resonant when I got lost for twenty minutes due to a lack of trail markers, poor online directions, and labyrinthine network of foot paths. But, hey, if you want to contemplate existentialism, then browse reasonably-priced sedans, this is the place for you.
Mansfield – Feels like there is more here to uncover, but we did dinner and drinks at Jimmy’s once and it was decent pub fare.
Marlboro – I have two friends who live in Marlboro. At one of their houses, I watched the Pats beat the Ravens in the AFC Title game on Cundiff’s missed kick. At the other house, I watched the Pats beat the Ravens in the playoffs in the Edelman double throw game. If we play the Ravens in the playoffs again anytime soon, a nice random Marlboro family might find me knocking at their door with a bucket of wings.
Mattapoisett – I’ve been to Ned’s Point Lighthouse a few times, most recently as a social distance outing with my parents. There’s a small beach, lots of boats, an a green area to run around, so I recommend it if you’re looking for something similar.
Medford – My friend Mike lives here. His oldest son is a few months younger than my oldest son, and the few times I’ve brought our kids by, I always feel like my kid is going to be a bad influence somehow, and then it works out fine. Again, normal parent concerns. He’s given me a list of venues I need to check out, so a return trip is in the works.
Mendon – My wife and I went to the Mendon Drive-In to see Guardians of the Galaxy. The fact that we were newly dating is the only context in which she’d agree to see Guardians of the Galaxy.
Middleboro – Took Griff to Oliver Mill Park right off rte 44. Cool park with many bridges, unfortunately because it was fall, the herring were not running.
Milford – This space previously talked about first kisses at a skating rink and hacky sacking at Burger King, but I’d be doing everyone a disservice if I didn’t put a spotlight on Basic Batch, which for my money is the best gourmet donut shop in the state, despite just opening in the middle of COVID.
Millville – We took a stroll down the Millville Lock trail, which has a neat bridge on it that the kids liked.
Monson – I got Keegan some ice cream at Westview Creamery. “Wow, great view you guys have here.” “Yeah, the sunsets are beautiful.” “Oh, so that must be facing west.” “Yeah…West…View.” “…Got it.” You can feed goats here, too. We also paid a brief visit to Vinica Brook Falls, which were really cool, but had no parking and a very narrow path with a steep drop off the side. Not great for a three-year-old.
Montgomery – I can’t say I’ve ever looked down on a hawk that was in-flight before, but that happened here at the top of Tekoa Mountain, which I hiked via the Grace Robson Sanctuary. Fortunate/unfortunately, I did not encounter any timber rattlers that supposedly reside here. That’s the Pike down below.
Nantucket – Hey, we did it! #351. My wife and I wrapped up this odyssey by celebrating our anniversary on Nantucket. We enjoyed the Cisco Brewery, loved our hotel room at the Nantucket Resort and Hotel, and enjoyed a variety of foods from Pi Pizzeria, Queequeg’s (tandoori butter and sushi FTW) and Kitty Murtaugh’s. It would’ve been nice if it was slightly warmer, but November definitely felt like a better time to be there than the heart of summer.
New Ashford – Above is the New Ashford Town Hall, which was locked up tight on a weekday because it’s the New Ashford Town Hall. Inside, however, is a black box that was used to cast the first vote for a woman in US History following women getting the right to vote. Next to the Town Hall, you can see half of the town’s mailboxes.
New Marlboro – Umpachene Falls was the perfect waterfall experience for my two small boys. Located in the back of a small park (so no hike required) and broken up into three tiers, it was never too fast that I was worried about my three-year-old being swept away, and it was never deeper than my thigh. Later, I discovered that it’s supposedly open to residents only, which is fine because we were guests…of…uh…Steve. Yes, Steve. Steve from New Marlboro.
Newburyport – I stopped at Michael’s for lunch with my parents on our way to Maine. While there, my friend Katie from college randomly texted me thinking she was texting her dad. It was amusingly awkward enough that we still refer to each other as family to this day. Above is the Chain Bridge that runs parallel to Rte 95 over the Merrimac River.
North Adams – Natural Bridge State Park is a small, but unique series of bridges and observation decks above a narrow chasm and white marble dam. We also had a great time grabbing dinner and ice cream at the open air food court at Mass MoCA (until witching hour hit the kids hard) and hiked the Cascades Trail that ends with a 50 foot waterfall in a keyhole shaped canyon that can only be accessed by hiking up through the brook itself.
North Brookfield – What does one do way out in North Brookfield you ask? Well, you check out the grave of MLB catcher turned murderer Marty Bergen, and tip your cap to Long View Recording Studio, the farm/studio that has played host to the likes of The Rolling Stones, J. Geils Band, and Yeah Yeah Yeahs.
Northboro – This was the only wedding I’ve been to so far where a guest threatened the bride’s brother. I believe this was also home to my first Wegman’s.
Norton – Kids love caves, so I was excited to find there was one so close to us, and King Philip’s Cave does not disappoint for exploring purposes at the end of a very short trail. The only drawback is that it is randomly off a small cul-de-sac in a wealthy area, practically sharing the property of a mansion. I imagine these well-to-do folks have looked out their windows once or twice and seen me scrambling after my three-year-old.
Oak Bluffs – Had a fluffy croissant from Back Door Donuts on my way to a very suspect bike rental. The area near the dock looked worth exploring and might be enough to make me forget about the bus driver who gave my middle schoolers an aggressive and strange lecture about “bullying” when they asked to sit in the same seats on the ride home from a game.
Orleans – If you want a sneaky town for a pub crawl, Orleans is it. I did one a few years back and there was about 5-6 establishments all within walking distance, and I think one or two new ones have popped up since. My favorite is an old standby, The Land Ho. Also, RIP The Baseball Shop, one of the last genuine baseball card shops. Try the Oreo Dream Bars from The Chocolate Sparrow like this happy customer above.
Palmer – I’m not clear on exactly how it happened, but I ended up with two ice creams at Rondeau’s Dairy Bar, and I think I lean Forest Lake Mud (coffee Oreo with chocolate swirls) over cotton candy.
Pelham – Buffam Falls is a cool sight in the winter – the water rushes in and out of view beneath brittle ice bridges – but would more navigable in warmer weather. The path was particularly slick on a day where it had been well-worn, but not quite melted.
Peru – This is what you see when you reach the GPS location for “Peru State Forest”. I’d blame the GPS, but this dirt road went for three miles in both directions with nothing indicating civilization or even marked trails. I’m afraid Peru has the ignominy of having the least going on of any town I’ve come across so far.
Pittsfield – The state tournament was here my senior year. I believe we affectionately referred to it as, “the town from Gummo.” I think I owe it a second, more mature trip. Update: Yeah…I’m still not moving here. But the woman at the Liberty Pizza counter was really nice.
Plympton – This is the future entrance to this year’s version of the Sauchuk Corn Maze. According to their web site (which features some very impressive pictures of past mazes) they have an “exclusive regional contract with the world’s largest regional cornfield maze company.” Not sure how I feel about corn mazes going corporate. They used to have more integrity. At least you’d have to be a moron to get stuck in a corn maze – the stalks grow like three feet apart. All you have to do is walk in a straight line through the “walls” to get out.
Quincy – My wife and I moved in together in a one bedroom apartment the size of a bird’s nest. I proposed at the end of Euclid Ave in the shadow of the hospital during a two foot blizzard that required me to resort to Plan C. We are so fond of Quincy that we spent our fourth anniversary bouncing around our old haunts – Southside, Cagney’s, Coop’s, The Fours. All that was missing was a bar pizza from the deceased S6.
Reading – I like Reading a lot; if I was to move to the north shore, it’s the first town I’d look up on Zillow to be disappointed by because no dots appeared in my price range. I stopped into Whitelam Books because screw Amazon (I’m not about to make a reading joke in Reading.)
Richmond – Balderdash Cellars is a winery overlooking a lake, and while I came in winter during COVID when it was to-go only, I’ve made a note to return in summer when it’s running full strength with its patio, food trucks, and live music.
Rockport – We stayed at the Rockport Inn and Suites for a wedding in Gloucester. There was an after party with a lot of pizza, and maybe balloon animals, but don’t quote me. We also went to Halibut State Park, which is pretty cool, but probably not the best place to let your dog or your three year old off the leash.
Royalston – There are three waterfalls in Royalston. The boys and I first attempted Royalston Falls, and I don’t care if it says it’s less than a two mile hike, I felt every step of that hike. The slope was arduous, the mosquitoes were cat-sized, and it was the first hike where the thought crossed my mind “if I sprain my ankle, I’m stuck out here alone with a three and a one year old.” It was that isolated. The second hike, Doane’s Falls, was much more accessible and enjoyable for me. The falls are by the road and the trail down the side gives many chances for a splendid view. So revived were we that we were about to attempt Spirit Falls when the weather kicked up nasty and looking at the topographical map, I realized I would be going straight up and down at one point coming or going and bailed. But I plan on going back at some point.
Salem – Tons of bars, history, and water views – I bet Salem is awesome in the spring before the onslaught of tourists, which lasts until Winter. I found solace at the Notch Brewery Biergarten, where I had my first smoky wheat ale, which had the singular taste of a Hoegaarden-flavor Black and Mild (I mean this in the best way possible.) I then found a hard to locate copy of a book from one of my favorite authors at Wicked Good Books, which in typical Salem fashion was half occupied by books in the occult/spiritual/fantasy realms.
Sandwich – The Heritage Museum and Gardens has a lot to offer different people – nature, art, classic cars, and so on. It’s a worthwhile way to spend a day outdoors on the Upper Cape., although unfortunately they do charge admission unlike many other natural sites I’ve been to.
Scituate – Does Humarock count if it doesn’t connect by land? Sure as heck does. A transformative spot in the summer for my teenage years, and one of the best 3rd of July parties you’ll find. Also, sorry Mrs. McGrath that I brought a stowaway to your cottage back in the summer of ’02.
Sheffield – The Ledge Trail at Bartholomew’s Cobble was perfect for two small kids at only half a mile long, tracing a massive boulder’s edge. We also spent time at the Thomas Reed UFO Monument Park, which some of you may recognize from Netflix’s Unsolved Mysteries. The Commonwealth actually dedicated this guy a park in acknowledgement of his alien abduction from the covered bridge above, which you can no longer drive through. I also got maple bourbon from Berkshire Distillers, and a surprisingly decent buffalo chicken sandwich from the Blue Door Cafe. I only say surprising because the clerk and I had tough start over the phone, but she won me over with small talk. The general store aesthetic of the place was exactly what you’d want from a small town in the Berkshires.
Shirley – Sometimes, the best subs come from the mom and pop local shops. That’s the case here with the Shirley Sub Shoppe. I went with the steak and cheese.
Somerset – Grabbed a Mad Mocha from the Pink Bean off Route 6. Quaint little coffee shop with outdoor seating, as well as additional seating in a greenhouse type area. The beverage was high quality as well.
Southampton – We stopped by Bashista Orchards for apple cider donuts and I sent the boys out into the fields to recover flotsam from Ted Kennedy’s 1964 plane crash across the street. No luck. We also got curbside wine for the lady of the house at Glendale Ridge Vineyards, which has a beautiful scenic overlook and offers a “tailgating” area for those who want to enjoy their purchase safely during COVID.
Southwick – We spent a couple hours at the Granville Gorge (yes, located in Southwick, not Granville, I was shocked and chagrined as well). This place was awesome for two small kids – shallow pools, fast streams, lots of rocks to throw. My only gripe is that I would humbly ask the teenagers of Southwick to pick up their broken bottles and bottle caps when they’re done. Oh, and I found the passerby who warned us of a bear sighting a bit unnerving.
Sterling – After purchasing ahead of time only to then spend 30 minutes baking in the sun while standing in line to get in, I was afraid that Davis Farmland was going to be Hillbilly Disney Hell. Thankfully, things improved once inside – Griff loved the tractor ride, water park, “Adventureland” and some (not all) of the animals.
Stoughton – Fear and Loathing in IKEA. Either we passed that Flurgg twice already and are lost, or I’m hallucinating on some bad Swedish meatballs.
Sudbury – Well, this a damn shame, or rather, a shameful dam. Ford’s Folly was constructed by the Henry Ford in the 1920s as part of a larger vision of a colonial-era village (you know, because Massachusetts doesn’t have any of those.) Thanks to faulty bedrock, however, the dam can’t hold any water, so the reservoir never gathered, and now it sits idly in the middle of the woods as the creek mockingly trickles beneath. Easily reached by trails either on Bigelow Drive or the end of Brimstone Lane.
Swampscott – I hit up Volo for the newest trend in pizza – Detroit-style. It’s similar to deep dish with the sauce on top of the cheese. It was a tad salty, but so hearty that I could’ve taken a solid nap after two slices.
Templeton – One of my favorite pictures I’ve ever taken is from Templeton. It’s a plain blue sign that says “The Mall at Templeton” but instead of having a mall behind it, it’s just a vacant, wooden lot. Somehow, they still have an Auntie Anne’s. Templeton!
Tolland – Mud, bugs, isolation…I would’ve enjoyed the Farmington River Walk in Tolland State Forest a little more if the trail cozied up to the river sooner, but for the entire first stretch, the river is out of view.
Truro – Despite having a satellite that looks “like a soccer ball,” the walk around the abandoned Truro Air Base and Jenny Lind Tower were a bit too much for tired, little legs.
Upton – Wedged between two houses on a cut-through street and tucked down behind a shed at Upton Heritage Park, the Upton Chamber is a dugout cave you can enter, perhaps built by natives or as a colonial root cellar. Red Rock Grill also has a great patio.
Wales – We had explored about 100 yards from the car at the Norcross Wildlife Sanctuary when the heavens opened up and we had to make a run for it. As far as Wales go, it ranks behind the deceased Hartford hockey team, but ahead of Voyage of the Mimi.
Ware – The Enfield Lookout is perhaps the best overhead view of the Quabbin Reservoir, which I attempted to show my son, but he had fallen asleep.
Warwick – Roads? Where we’re going, we don’t need (paved) roads. I spent an hour trying to track down the location of the Brotherhood of the Spirit commune (the original hippie commune) on the dirt roads of Warwick and the best I could do was an overgrown plot with a greyhound and VW Bus abandoned near the road. Either I was successful or lucky to get away alive. We also had a pleasant picnic at the foot of Mt. Grace.
Wayland – I’ve stopped at the Coach Grill for a beer a handful of times while waiting for coaches meetings to start. I can’t speak to the food, but I do know that I’ve never not been the worst dressed person in the room.
Wellfleet – When I was six, my family went to the Welfleet Drive-In to see “Honey, I Shrunk the Kids”. I don’t remember why, but I was a royal pain in the ass the entire time. Kicking seats. Whining,. Annoying my sister. Just human misery. Then on our way out, I said, “That was fun, let’s do it again.” And that was the closest I ever came to being murdered by my family. (Don’t worry, my oldest is definitely less than three years from a stunt like this.) Update: I just reread the double feature and started chuckling. Only drive-ins do the “one for the kids, then one for the adults” format. “Tonight, we’ll be featuring Trolls World Tour, followed by The Last House on the Left”
West Boylston – The Old Stone Church, remnants of a town that was flooded to create the Wachusett Reservoir, is a very cool landmark. From the bridge, it looks like a serene location for an outdoor wedding, and upon closer inspection, it was a fun area for my kids to run around – so long as they avoided the empty nips and broken beer bottles in the back of the church.
West Newbury – I can’t say enough good things about Long Hill Orchard Farm. After our picnic, they gave my son an extra brownie and oreos on his ice cream, plus some stickers for the hell of it. Oh, and they sell small meatball subs for $1.25, which it would be wrong not to take advantage of. Finally, I appreciate that they have Jolly Rancher as an ice cream topping, which I assume ordering gets you on a government watch list, so they’re doing their part to look out for America. Apropos – we drove by John Cena’s boyhood home.
West Tisbury – One of the handful of massive trees with recumbent limbs, this one on the corner of North Street had a sign that said “Historic Tree Do Not Climb”. But as best as I can find, the only reason it’s “historic” is that people keep taking pictures of it. So, absent of a real story, I’m forced to make one up: This is the tree that Martha fell from and got amnesia, thus giving the island it’s name.
Westford – Kimball Farm is still on the to-do list, but today, I’d like to talk with you about The Westford Knight. A rock slab with lines carved into it vaguely in the shape of a sword has somehow given shape to a story about the Knights Templar predating Columbus’s arrival or whatever. I don’t see it. The sleeping bronze guy is a bigger attraction. Why, in Massachusetts, do we love our obscure rock carvings so?
Weston – There was a time where I was a bachelor just starting out in my teaching career so I had a lot of extra time but not much extra income which added up to many cheap rounds of golf at Leo J. Martin golf course aka the giant sandtrap. The irony of the cheapest public course being located in one of the wealthiest towns is not lost on me.
Weymouth – I met my wife’s friend at The Next Page for the first time. An hour later, she offered me her colostrum. That’s how she rolls. Oh, the bar pizza was good, too.
Wilbraham – Rice Farm offers a little bit of everything and has that welcoming center of the community feel to it. My only gripe was how small the parking spots are, which seems petty unless you’re juggling two kids and the person in the car next to you is watching like a hawk. I also tried to go to Pop’s Biscotti and Chocolate Shop, but we might need to put an APB out for Pop’s – the people at the coffee shop next door said they hadn’t seen any activity over there in months, despite them still being listed as open online. Hopefully everyone is okay and they are not another economic victim of COVID.
Wilmington – This is the remnants of the Shawsheen Aquaduct, which straddles the river of the same name, dividing Wilmington from Billerica.
Windsor – The first bad sign was that upon entering Windsor, all pavement disappeared, and I saw signs advertising that Windsor “now had internet.” Hopefully, by next year, they’ll have access to beepers. After an adventure through the woods, we did find the hard to locate Windsor Jambs trail, a short hike that parallels a deep, narrow series of cascades which are obscured by a (very necessary) fence that lines the cliff.
Worcester – The WooSox and Polar Park have been an awesome addition to the city in their first year of existence – but if you visit, try to patron the restaurants and bars on Green Street before or after. The parking crunch with the new ballpark has actually made things harder for some of these places to get business.
Yarmouth – Nothing speaks to the summer of my childhood quite so much as Pirate’s Cove. Did I sully that memory by playing a skins game for $3 a hole a few years back? No, because I probably cheated at mini golf as a kid anyway. “How many strokes was that, Alex? Six?” “No, I think it was only four…”
Plainville – Look at that. I forgot Plainville, the town directly south of me. So it’s at the end. I’ll give Plainville four shoutouts – Rancho Chico is our go to for Mexican, Don’s Diner does killer pancakes, Summer Scoop combines outdoor seating with ice cream, and The Chieftain is one of the better Irish pubs in the area. Oh, and the pic above is from An Unlikely Story, a vibrant local book store
  • The 7 Natural Wonders of Massachusetts
  • 1. Tannery Falls – Savoy
  • 2. Purgatory Chasm – Sutton
  • 3. Chesterfield Gorge – Chesterfield
  • 4. Sunderland Caves – Sunderland
  • 5. Farley Ledges – Erving
  • 6. Outer Beach – Chatham/Orleans
  • 7. Mount Greylock – Adams
  • 7 More Natural Wonders of Massachusetts
  • 1. Twin Cascades – Florida
  • 2. Tekoa Mountain – Montgomery/Westfield
  • 3. Douglas State Forest – Dougles
  • 4. Natural Bridge State Park – North Adams
  • 5. The Butterball Tree – Sunderland
  • 6. The Cascade – Adams
  • 7. Rock House Reservation – West Brookfield
  • The 7 Man-Made Wonders of Massachusetts
  • 1. Hoosac Tunnel – Florida/Adams
  • 2. Dogtown Commons – Gloucester
  • 3. Battleship Cove – Fall River
  • 4. Fenway Park – Boston
  • 5. DeCordove Sculpture Garden – Lincoln
  • 6. Ashintully Gardens – Tyringham
  • 7. Crane Estate – Ipswich
  • 7 More Man-Made Wonders of Massachusetts
  • 1. French King Bridge – Erving
  • 2. Becket Quarry – Becket
  • 3. Keystone Arches – Middlefield
  • 4. Three Sisters Sanctuary – Goshen
  • 5. Tower Hill Botanic Gardens – Boylston
  • 6. Barges Beach – Gosnold
  • 7. Bridge of Flowers – Shelburne
  • 10 Towns I Need to Revisit
  • 1. Amesbury
  • 2. North Adams
  • 3. Webster
  • 4. Easthampton
  • 5. Salem
  • 6. Hudson
  • 7. Bernardston
  • 8. Williamstown
  • 9. Northampton
  • 10. Woburn
  • Five Places I Probably Never Need to Go Again
  • 1. Peru State Forest – Peru
  • 2. Sampson’s Pebble – Oakham
  • 3. Truro Air Base – Truro
  • 4. Salisbury Beach – Salisbury
  • 5. The Bicentennial Chair – Gardner
  • Five Random Graves
  • 1. Author William Styron – Tisbury
  • 2. Guy with a Beard, Joseph Palmer – Leominster
  • 3. MLB Pitcher Jack Chesbro – Conway
  • 4. Poet Archibald MacLeish – Conway
  • 5. John Belushi – Chilmark
  • Best Discoveries: Ice Cream
  • 1. Mt. Tom Ice Cream – Easthampton
  • 2. Ice Cream Cafe – Orleans
  • 3. Sullivan Farms – Tyngsboro
  • 4. Richardson’s – Middleton
  • 5. Crescent Ridge – Sharon
  • 6. West End Creamery – West Newbury
  • 7. Heidi Hollow – Hanson
  • Best Discoveries: Pizza Places
  • 1. All of Dracut
  • 2. Lynwood Cafe – Randolph
  • 3. Volo – Swampscott
  • 4. Casa Pizzeria – Ludlow
  • 5. Pi Pizzeria – Nantucket
  • 6. Venus II – Marshfield
  • 7. Hot Tomatoes – Williamstown
  • Best Discoveries: Pubs/Breweries
  • 1. Stone Cow Brewery – Barre
  • 2. Lucky Dawg Pub – Pembroke
  • 3. Notch Brewery – Salem
  • 4. Timberyard Brewery – East Brookfield
  • 5. Boiler Bar – Orange
  • 6. Munich Haus – Chicopee
  • 7. Red Apple Farm – Phillipston
  • 8. Olde Forge – Lanesboro
  • Best Discoveries: Spend a Day with the Kids
  • 1. Discovery Museum – Acton
  • 2. Chapel Falls – Ashfield
  • 3. Glendale Falls – Middlefield
  • 4. Granville Gorge – Southwick
  • 5. Pirone Park – Ayer
  • 6. Moore State Park – Paxton
  • 7. Polar Park – Worcester
  • 8. Beyond Full – Hopedale
  • 9. Battleship Cove – Fall River
  • 10. Trap Falls – Ashby
  • Best BBQ Places
  • 1. Theodore’s – Springfield
  • 2. 2 Jerks BBQ – Raynham
  • 3. BT’s Smokehouse – Sturbridge
  • 4. Kinfolk BBQ – Taunton
  • 5. Blue Ribbon BBQ – Newton
  • Neighborhoods/Villages People Think are Official Towns, but Aren’t
  • 1. Vineyard Haven (Tisbury)
  • 2. Florence (Northampton)
  • 3. Whitinsville (Northbridge)
  • 4. Devens (Ayer/Shirley/Fort Devens)
  • 5. Cochituate (Framingham? Sudbury?)
  • 6. Turner Falls (Montague)
  • 7. Baldwinville (Templeton)
  • 8. Onset (Wareham)
  • 9. Hyannis (Barnstable)
  • 10. Cuttyhunk (Gosnold)

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