10 Most Charming Small Towns in Massachusetts


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Massachusetts is known for a lot of things, like its delicious clam chowder, gorgeous fall foliage, and rich history. It’s also known for having incredibly charming small towns that are simply perfect. Everything from the unique architecture to the cozy local shops make a lasting impression. There are so many Bay State small towns worthy of visiting, though; how do you narrow down which ones to visit first? 

Don’t worry, that’s where we step in. Here are 10 of the most charming small towns in Massachusetts to visit: 

Concord

Historic bridge in the fall next to water

County: Middlesex 

Population: 17,668 (as of 2010) 

Compared to its southeastern neighbor, Boston, the town of Concord is considered a small one! This charming town was founded in 1635 and has historical roots in the American Revolution. It’s also said that literary greats Ralph Waldo Emerson and Henry David Thoreau hung out at Walden Pond. With that kind of history and draw, you know there has to be something charming about it. 

It’s easy to see why Concord is one of the most charming Massachusetts small towns. It’s the quintessential New England town that has a healthy mix of picturesque living and beautiful nature. If you plan on heading here, check out North Bridge (where “the shot heard ‘round the world” in the Revolutionary War happened) or lounge on Walden Pond.

There are also plenty of restaurants to stop at while taking in all Concord has to offer. A trip here is one embedded in history and culture—and it’s one you’ll want to make again. 

Rockport

Boats floating on the water next to a red building

County: Essex County 

Population: 6,952 (as of 2010) 

Is there anything more charming than a small seaside New England town? Head to Rockport in Essex County to get your fix of Massachusetts charm. It’s only an hour north of Boston, but it feels like you’re in another world.

There’s plenty to do in this town, like kayaking along Cape Ann, exploring the Rockport quarries, and even visiting a local art gallery. One of the things you must do is visit Motif #1. It’s a red replica of an old fishing shack located on Bradley Wharf. It’s an iconic building known around the world, especially in the art community. 

Since you’d be in a seaside Massachusetts town, it’s only fitting that you indulge in some seafood. Some places to check out include Roy Moore Lobster Co., The Lobster Pool, and Brackett’s Oceanview Restaurant. Stop in to dig in! 

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Great Barrington

View of the mountains next to rocks

County: Berkshire 

Population: 6,852 (as of 2018) 

You’ll find this incredibly charming small town in the valley of the Housatonic River in southwestern Massachusetts. Great Barrington defines a picturesque town, from its adorable downtown area to the beautiful nature that surrounds it. The downtown area is also home to multiple cultural and historic spots, including the Mahaiwe Performing Arts Center

Head downtown to indulge in Great Barrington’s restaurant and retail scene. Then, head out for a scenic hike at Monument Mountain Reservation or the Housatonic Flats Reserve for a nice hike in the beautiful Berkshires. Grab your camera and capture as many memories of this trip as you can! 

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Stockbridge

River next to buildings in winter

County: Berkshire

Population: 1,947 (as of 2010)

If you find yourself in the Berkshires, don’t forget to stop and explore the wonderfully charming small town of Stockbridge. Stockbridge is just a quick 13 minute drive from Great Barrington, and the short drive is well worth it. Stockbridge is an adorable small town with charming architecture that has that quintessential New England feel to it.

You’ll see historical buildings and lovely small businesses as you stroll down picturesque Main Street, where you can shop around and get to know the area. Visit the area around Christmas and you’ll see Main Street transform into a true winter wonderland. 

One of the places you must stop to see in Stockbridge is the Norman Rockwell Museum. Norman Rockwell was a famous artist who created incredible art that reflected American culture. He created the covers for The Saturday Evening Post magazine for decades before passing away in 1978. He was a resident of Stockbridge, and as such, it’s only fitting you can travel to the town to see his work. 

Other activities to do in Stockbridge include visiting Naumkeag Public Garden and hiking along the Laurel Hill Association trails. There’s a little bit of something for everyone in Stockbridge! 

Provincetown

Beach in Provincetown with sand

County: Barnstable 

Population: 2,994 (as of 2011)

Head to Cape Cod to get a glimpse of this charming seaside small town. Provincetown, also known as P-Town, is located on the northern tip of the cape and is a popular summer destination in the Bay State. It has some of Massachusetts’ best beaches, including Race Point Beach and Herring Cove Beach

In addition to being a great beach town, Provincetown is known for having an impressive art scene. You’ll find these galleries along Commercial Street, where you can walk along and pop into each gallery. Commercial Street is also an incredible street to walk down and shop along.

Grab lunch at one of the restaurants lined along the street and poke around in the shops until you find the perfect thing to remember your trip to Provincetown. Expect to see a lot of foot traffic in the summer, though, as that’s the busiest time in P-Town.  

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Oak Bluffs

Aerial view of a lake with boats on it surrounded by land

County: Dukes (on Martha’s Vineyard) 

Population: 4,678 (as of 2018)

Located on the idyllic Massachusetts island of Martha’s Vineyard, Oak Bluffs is a charming small town rich with history and culture, especially African American culture. It’s a top tourist destination in the summer, so if you’re looking to go during a quieter time, try going in late fall or winter. 

A trip to Oak Bluffs is sure to be a trip you won’t soon forget. Once you get there, head to one of its lovely beaches like Oak Bluffs Town Beach or Inkwell Beach. Then, make sure you head to an Oak Bluffs iconic landmark: The Flying Carousel.

The Flying Carousel is truly a piece of history, as it’s the oldest operating platform carousel in the United States. It was originally in New York City but moved to Martha’s Vineyard in the 1880s. It’s a favorite landmark for tourists and locals alike, so add it to your must-see list on this trip. Then, head to Circuit Avenue to poke around charming local restaurants and shops. 

Chatham

Chatham Lighthouse under a blue sky, Small Towns in Massachusetts

County: Barnstable

Population: 6,125 ( as of 2010)

Head to the southeastern part of Cape Cod to experience this charming small town. Chatham is a lovely seaside town that has plenty of beaches to explore. One of the coolest ones to visit is Lighthouse Beach, located near the historic Chatham Lighthouse. It’s one of the 16 remaining lighthouses on the Cape Cod coast, so make sure you head there to see a unique piece of history. 

Some other things to do in this charming cape town include visiting the Monomoy National Wildlife Refuge, seeing the Steve Lyons Art Gallery, and taking a stroll through the Chatham Railroad Museum. Everyone in the family will find something they’d like to do! 

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Lenox

Historic white estate under a blue sky

County: Berkshire 

Population: 5,025 ( as of 2010)

Add Lenox to your list of must-visit small towns in Berkshire County. This lovely and scenic small town is just 10 minutes away from Stockbridge, so you can easily go from one town to the next. There are plenty of fun things to do in Lenox, like visiting the Ventfort Hall Mansion and catching a show at the popular Tanglewood, known for being the summer home of the Boston Symphony Orchestra. 

You’ll also find lovely boutiques and stores to shop at in Lenox. If you’re in need of a nature fix, walk through Kennedy Park or Parsons Marsh Reserve to become one with the Berkshire beauty. 

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Hadley

View of a river with green trees

County: Hampshire 

Population: 5,346 (as of 2018)

Massachusetts charm takes hold in this adorable small town. Hadley is a wonderful place to stroll through, especially if you’re looking to get lost in nature for a bit.

Skinner State Park is a top place to visit; there, you’ll see incredible views of the Connecticut River Valley while walking through beautiful trails. There are other activities to do within the park too, including mountain biking and even hang gliding. 

Other things to do in Hadley include visiting the New England Falconry and the Hadley Farm Museum. Add them to your list of activities and experience the great charm Hadley has to offer. 

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Sturbridge

Old brown building next to a river

County: Worcester

Population: 9,640 (as of 2018)

You’ll get a nice dose of New England historic charm during a trip to Sturbridge. One of the most interesting things to check out is the Old Sturbridge Village, a living museum that depicts what New England life was like in the late 18th and early 19th centuries. You can literally step into another era and see what life was like before electricity. 

If you prefer more modern activities, Sturbridge has plenty of other things to do. You can visit the Hyland Orchard and Brewery or catch a show at the Stageloft Repertory Theater. You’ll be planning your next trip to this charming small town before you know it! 


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