You think you know Massachusetts. You’ve seen the postcards of the swan boats in Boston or the "Hocus Pocus" houses in Salem. But honestly, the way people talk about cities and towns in Massachusetts usually misses the point. It’s not just a collection of historical markers and Dunkin’ drive-thrus. It’s a messy, fascinating patchwork of 351 distinct municipalities where the local politics are a blood sport and the "town" you’re standing in might actually be a city in disguise.
Massachusetts is weird. Legally, every square inch of the state belongs to one of these 351 communities. There is no "unincorporated" land here. If you’re in the woods, you’re in a town. If you’re on a mountain, you’re in a town. And if you ask a local where they’re from, they won’t say "Massachusetts"—they’ll name a specific neighborhood or a town you’ve never heard of, like Belchertown or Florida (yes, we have one of those, and it’s usually covered in snow).
The Great Identity Crisis: Is it a City or a Town?
Here is the thing: in the Bay State, the difference between a city and a town isn't about how many Starbucks there are. It’s about the form of government. Basically, a town is governed by a "Town Meeting," which is exactly what it sounds like—a giant, sometimes chaotic gathering where neighbors argue about the school budget until 11:00 PM on a Tuesday.
A city, on the other hand, has a mayor or a city council.
But it gets confusing. Towns like Amherst, Agawam, and Weymouth actually have city-style governments, but they legally kept "Town" in their name because they liked the vibe. Meanwhile, North Adams is the smallest city in the state with only about 13,000 people. Brookline is a "town," but it has over 63,000 residents, making it bigger than many of our actual cities. It's quirky. It's confusing. It's very Massachusetts.
Coastal Gems vs. The Western Wilds
Most visitors stick to the coast. You’ve got Boston, which is the obvious heavy hitter. It’s got the history, the T (our subway that’s the oldest in the country), and that specific brand of "aggressive-friendly" hospitality.
Then there’s Salem. Look, Salem is great, but try going there in October. It’s basically the Disney World of the occult. If you want the real North Shore experience without the three-hour wait for a sandwich, check out Gloucester or Rockport. In Rockport, you’ll find "Motif #1," a little red fishing shack that is supposedly the most painted building in the world. Honestly, it’s just a shack, but against the Atlantic backdrop, you sort of get the hype.
If you head south, you hit Plymouth. Everyone goes to see the Rock. Spoiler alert: the Rock is small. It’s in a pit. It’s a rock. But the town itself? Stunning. The waterfront has this salty, old-world energy that feels authentic. Further out is New Bedford, once the whaling capital of the world. It’s grittier than the Cape, but if you want the best seafood of your life and a real sense of maritime history, it’s the place to be.
The "Hidden" Massachusetts
- The Berkshires: This is where the wealthy Bostonians and New Yorkers go to pretend they like nature. Towns like Lenox and Stockbridge are picture-perfect. Think Norman Rockwell paintings (because he lived there).
- The Pioneer Valley: This is "Middle Massachusetts." Towns like Northampton and Amherst are college hubs. It’s where you go for independent bookstores, vegan cafes, and people wearing Birkenstocks in January.
- The Quabbin Reservoir: Ever heard of the "Lost Towns"? In the 1930s, the state literally wiped four towns (Dana, Enfield, Greenwich, and Prescott) off the map to build a reservoir for Boston’s water. You can still hike to some of the old cellar holes. It’s eerie as hell.
Why 2026 is Changing the Map
Right now, in 2026, we’re seeing a weird shift. For a long time, everyone was fleeing the small towns for the tech hubs. But with the cost of living in Boston hitting "sell your kidney" levels, people are migrating to places like Worcester and Lowell.
Worcester is having a massive moment. People used to make fun of it, calling it "The Woo," but with the new Polar Park and a booming biotech scene, it’s legitimately cool now. And Revere? It was the fastest-growing large municipality recently. It’s not just a beach town anymore; it’s becoming a serious extension of the Boston skyline.
What Most People Miss About the 351
The real magic of cities and towns in Massachusetts isn't in the big landmarks. It’s in the hyper-local stuff.
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It’s the fact that Quincy is the birthplace of two presidents and Dunkin' Donuts.
It’s the fact that Webster has a lake with a name so long ($Lake Chargoggagoggmanchauggagoggchaubunagungamaugg$) that nobody can actually pronounce it, so we just call it Webster Lake.
It’s the "paper cities" like Holyoke and Lawrence that were the Silicon Valleys of the 19th century, with their massive brick mills now being turned into trendy lofts and breweries.
Actionable Advice for Navigating the Bay State
If you’re planning to explore, don't just "go to Massachusetts." Pick a region and commit.
- Skip the tourist traps: If you want a beach day, skip the crowded parts of Cape Cod and head to Crane Beach in Ipswich. The dunes look like something out of a movie.
- Eat like a local: You haven't lived until you've had a North Shore roast beef sandwich. Look for places in towns like Danvers or Peabody. It’s not a deli sandwich; it’s a lifestyle.
- Check the calendar: If you visit a town during their "Annual Town Meeting," stay away from the school gym unless you want to hear a two-hour debate about a specific stoplight.
- Use the Commuter Rail: You can get to places like Salem, Concord, and Lowell from Boston’s North or South Station for a few bucks. It beats fighting traffic on Route 128, which is basically a parking lot designed by demons.
Massachusetts is a state of contradictions. It’s the birthplace of the Revolution and the home of the most stubborn "we’ve always done it this way" attitudes you’ll ever encounter. Whether you’re walking the cobblestones of Nantucket or the industrial streets of Fitchburg, you’re stepping into a story that’s been writing itself for 400 years.
Your next move: Download the "MBTA mTicket" app if you're staying near Boston, or grab a physical paper map of the Berkshires—cell service gets spotty out near Mount Greylock, and you don't want to get lost in a town that doesn't even have a stoplight.