10 Charming Small Towns to Visit in Massachusetts

From the coast to the hills, these are the best small towns to visit in Massachusetts.

Massachusetts is home to nearly seven million residents sprinkled across 10,565 square miles, but not everyone lives in its bustling metropolises like Boston, Worcester, and Springfield. The state is punctuated by hundreds of smaller towns that are worth exploring, from charming coastal villages to historic mountain towns.

“With 351 cities and towns across the Commonwealth, the small towns of Massachusetts are bursting with history, culture, innovation, cuisine, and natural beauty,” Maria Speridakos, the director of international public relations at the Massachusetts Office of Travel and Tourism, shared with Travel + Leisure. “Visitors love to explore our seaside towns and fishing villages along the coast, from north of Boston down to the Cape and Islands and southeastern Massachusetts. And they love our charming small towns nestled in the rural byways and mountains of Central and Western Massachusetts, and the historic towns in the Merrimack Valley and Pioneer Valley.”

And, as Speridakos added, these places make for spectacular getaways no matter the time of year.

“Massachusetts small towns are in vogue all four seasons, from spring getaways and summer vacations to fall foliage and winter outdoor adventures, ” Speridakos said.

Want to get to know the state’s quaint communities a little better? Here are 10 small towns in Massachusetts worthy of planning an entire trip around.

Related: 20 Best Weekend Getaways in New England

Provincetown

Located at the very tip of Cape Cod, Provincetown has long been a summertime hot spot for Massachusetts residents and out-of-state tourists alike. And though it’s a rather famous spot, it’s still a small town, with fewer than 3,000 people calling it home year round. Come enjoy its beaches, its beloved Pride events, and its arts and culture scene, including its numerous galleries that are fantastic in summer, fall, winter, and spring.

Concord

Located just 20 miles outside of Boston, Concord is one of the state’s most accessible small towns. The community is best known for its divine outdoor spaces like Walden Pond, which inspired some great American writers, including Henry David Thoreau and Ralph Waldo Emerson, who both called Concord home.

Northampton

Northampton is perhaps the “largest” of the small towns on the list with some 29,000 residents, but that doesn’t make it any less charming. Located in the western half of the state, this town has a rich arts scene (visit the Northampton Museum and Art Gallery), local shops, and several music venues offering live performances.

Rockport

Back on the east coast of Massachusetts, travelers can explore Rockport, an adorable town of fewer than 8,000 residents at the tip of Essex County. The town offers year-round dining and shopping options, as well as plentiful beach and woodland hikes for those looking to get out and explore Mother Nature.

Williamstown

Tucked in the northernmost corner of the state, travelers will find the adorable community of Williamstown. It’s another small but mighty presence in the art world thanks to the Clark Art Institute, which showcases impressionist and contemporary artworks throughout the year. The town may also be familiar to hikers, as it’s located directly on the Appalachian Trail.

Sandwich

Make your way out to the Cape to visit Sandwich, the oldest community on the peninsula. With age comes both beauty and history; guests can visit historical landmarks like the Hoxie House Museum, a home built around 1675 that is likely the oldest saltbox home on Cape Cod. The Heritage Museums and Gardens and the famed Sandwich Glass Museum are also worth visiting.

Stockbridge

Have a picture-perfect getaway in Stockbridge. This teeny town in the Berkshires is so gorgeous, it inspired the great American painter and resident, Norman Rockwell. Come here to explore the lush natural landscapes or the more curated flora at the Berkshire Botanical Garden, and don’t miss the chance to see a show put on by the Berkshire Theatre Group.

Oak Bluffs

Put your toes in the sand when you visit Oak Bluffs, a quaint little town on the island of Martha’s Vineyard. The community is perhaps best known for Joseph Sylvia State Beach, a two-mile-long beach made famous in “Jaws.” The community also happens to be an A-list haven, counting the Obamas as summertime regulars.

Nantucket

Take one more island escape by visiting Nantucket, an isolated island past Martha’s Vineyard. Home to a little over 11,000 full-time residents, the island is certainly small, but it too packs a wallop when it comes to history. Specifically, visitors here can check out three historic lighthouses: Great Point, Sankaty Head, and Brant Point. Travelers will also be delighted by the bountiful seafood spots to enjoy here, as well as some rather excellent boutique shopping.

Westford

Did you know you can ski in Massachusetts? Just head to the town of Westford to see for yourself. Located in the northern part of the state close to the New Hampshire border, visitors can hit the slopes at the Nashoba Valley Ski Area. Of course, it’s a year-round destination, thanks to its hiking and biking trails and sights like The Butterfly Place, an indoor living environment for butterflies from all over the globe.

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