Massachusetts is certainly not lacking in charm. You can pretty much spot a picturesque white steeple, historic building, or gorgeous ocean sunset anywhere you go. These towns just kick it up a notch. Check these quaint towns in Massachusetts for your daily dose of nostalgia and classic New England beauty.

1. Stockbridge
Stockbridge, MA, USA
Flickr/Massachusetts Office of Travel and Tourism
No list of small towns in Massachusetts (or America, for that matter) would be complete without Stockbridge. This is the town Norman Rockwell used as a model. If that doesn't convince you that this place is loaded with charm, go visit for yourself. Book a room at The Red Lion Inn (built in 1773) and grab an old-fashioned meal at the Elm Street Market lunch counter.
2. Hadley
Hadley, MA, USA
Flickr/Massachusetts Office of Travel and Tourism
Man, Hadley, Massachusetts, is pretty. The landscape of Hadley is largely open-field farming, which is so unique in Massachusetts as that kind of farming largely ended in the 18th century. The "Cultural Landscape of Hadley, Massachusetts" is actually on the World Monuments Fund's watchlist for endangered sites. Go take in the beauty and charm of Hadley while you still can!
3. Rockport
Rockport, MA, USA
Flickr/Massachusetts Office of Travel and Tourism, by Tim Grafft
Cape Cod isn't the only place to find charming seaside spots in Massachusetts -- we absolutely adore Rockport! Stroll around the Bearskin Neck area and don't miss The Paper House, a real house constructed out of actual newspaper.
4. Westford
Westford, MA 01886, USA
Flickr/Massachusetts Office of Travel and Tourism
So the town of Westford might be a slightly larger small town with a population of over 24,000, but this place definitely has that small-town feel. Spend some time on the slopes at the local Nashoba Valley ski resort and check out the Westford Academy's bell tower – that bell was made by Paul Revere!
5. Newburyport
Newburyport, MA, USA
Flickr/Massachusetts Office of Travel and Tourism
This cute town in Massachusetts is dripping with quaintness. Have a stroll down State Street and enjoy an ice cream in Market Square. If antiquing is your game (or you just love funky doodads) you need to visit Oldie's Marketplace. It's a giant barn absolutely crammed with all sorts of oddities and treasures.

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6. Rowe
Rowe, MA, USA
Flickr/Massachusetts Office of Tourism and Travel
Forget being a small town – Rowe is more like a micro-town. With a population of 393, this sleepy spot is perfect for getting away from the bustle of urban life. Splash around in Pelham Lake and enjoy the classic New England scenery. A great place for hiking, fishing, hunting, canoeing, and kayaking.
7. Oak Bluffs
Oak Bluffs, MA, USA
Flickr/Massachusetts Office of Travel and Tourism
Nestled on the northeastern shore of Martha’s Vineyard, this picturesque small town in Massachusetts features an incredible seaside park (Ocean Park) and a cluster of fairytale-style "gingerbread houses." Be sure to have a spin on the Flying Horses Carousel, which is the oldest in the nation. Fun for junior gallopers and veteran jockeys alike.
8. Provincetown
Provincetown, MA, USA
Flickr/Massachusetts Office of Travel and Tourism
Provincetown isn't exactly a hidden gem. This art colony's population can swell to over 60,000 in the summer, but its year-round population is actually only 2.9k! Come here for the shops, galleries, and LGBT-friendly celebrations. Grab lunch at The Lobster Pot and soak up some sunshine at Race Point Beach.
9. Lenox
Lenox, MA, USA
Flickr/Massachusetts Office of Travel and Tourism
Lenox is a sweet Massachusetts town that's perhaps best-known as the site of Tanglewood -- the summer home of the Boston Symphony Orchestra. A visit to Lenox would not be complete without dropping by to marvel at the estate. Though if you'd prefer to just spend the day riding around town in a horse-drawn carriage, I totally get that.
10. Concord
Concord, MA, USA
Flickr/Massachusetts Office of Travel and Tourism
This town of Concord, Massachusetts, was the site of The Battle of Lexington and Concord, the first battle of the American Revolution. Home to Minuteman National Historic Park (prime picnic real estate) and Walden Pond (Henry David Thoreau thought this was a pretty cool place), Concord is brimming with old-fashioned charm.

Whether you’re looking for a scenic drive or an extended stay in a charming locale, these spots have you covered. What are your favorite quaint small towns in Massachusetts? Share them with us below!

If you’re looking for some small towns in Massachusetts that are also super walkable, these little locales all boast amazing Main Streets and downtown districts!

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Quaint small towns in Massachusetts

Sarah M. | September 20, 2022

What's the friendliest small town in Massachusetts?

Named one of the friendliest towns in America by numerous publications over the years, Provincetown is such an open-minded and friendly place where everyone is meant to feel welcome. The year-round population of Provincetown hovers around 3,000 people, but in the summer, the population explodes to a whopping 60,000. Despite this big population boom each summer, Provincetown retains its small-town charm and welcoming spirit all year round. Regardless of the time of year you visit, you'll encounter historical sites, galleries, museums, plenty of dining options, and cafes on and around Commercial Street. The town is also near a ton of amazing outdoor recreation: perhaps you'll hike in the Province Lands, swim or sunbathe at one of the beaches, bike along the Province Lands Bike Trail, charter a boat, or even go whale watching. You can do it all in this quaint Massachusetts town!

What are the best small town Main Streets in Massachusetts?

We firmly believe that the heart and soul of Massachusetts is in its small towns, something you will discover when you visit charming locales like Concord, Provincetown, Falmouth, Rockport, Great Barrington, and Amherst. With regard to Amherst, you'll love the local shopping opportunities in this downtown district. With book and record shops, a vintage store, a bike shop, and an instrument shop among others, there's quite the eclectic mix of places to browse. There's also quite a bit of culture to experience at the museums, galleries, and cinema and you'll love the culinary options offered here as well. So plan a weekend trip here, or make it part of a fun road trip in Massachusetts.

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