Explore the best small towns in Massachusetts, perfect for year-round getaways and rich in history, culture, and natural beauty.
Massachusetts is home to nearly seven million residents scattered across 10,565 square miles, yet it boasts countless small towns worth exploring. From charming coastal villages to historic mountain communities, the state is rich in unique destinations.
Maria Speridakos, the director of international public relations at the Massachusetts Office of Travel and Tourism, emphasizes that “the small towns of Massachusetts are teeming with history, culture, innovation, cuisine, and natural beauty.” She adds that “visitors love to explore our seaside towns and fishing villages along the coast, from north of Boston all the way to Cape Cod and the Islands.” Moreover, quaint towns nestled in rural roads and the mountains of Central and Western Massachusetts offer countless year-round activities.
Speridakos highlights the allure of Massachusetts’ small towns throughout the seasons, making them perfect for spring getaways, summer vacations, scenic fall foliage, and winter outdoor adventures. Ready to explore these quaint communities? Below are ten small towns in Massachusetts worthy of your next trip.
01. Provincetown
Located at the very tip of Cape Cod, Provincetown has long been a summer hotspot for residents and tourists alike. With a population of fewer than 3,000 year-round, visitors enjoy its stunning beaches, vibrant Pride events, and a rich arts culture. It boasts numerous galleries that are appealing throughout the year.
02. Concord
Just 20 miles from Boston, Concord is one of Massachusetts’ most accessible small towns. Best known for its beautiful outdoor spaces, such as Walden Pond, it inspired renowned American writers like Henry David Thoreau and Ralph Waldo Emerson, both of whom resided in Concord.
03. Northampton
Northampton, with approximately 29,000 residents, is one of the largest towns on this list yet remains incredibly charming. Located in the western part of the state, it features a thriving arts scene, local shops, and various music venues hosting live performances.
04. Rockport
On the east coast, travelers can discover Rockport, a quaint town boasting fewer than 8,000 residents. Known for its year-round dining and shopping, it offers numerous beach trails and woodland hikes that beckon nature enthusiasts.
05. Williamstown
Located in the northern corner of Massachusetts, Williamstown is home to the Clark Art Institute, which displays impressionist and contemporary artworks year-round. Additionally, it is situated along the Appalachian Trail, making it popular among hikers.
06. Sandwich
Visit Sandwich, the oldest community on Cape Cod, where history and beauty intertwine. Guests can explore landmarks like the Hoxie House Museum, believed to be the oldest saltbox home on the Cape, alongside the Heritage Museums and Gardens and the renowned Sandwich Glass Museum.
07. Stockbridge
Discover Stockbridge, a picturesque town in the Berkshires that inspired painter Norman Rockwell. Visitors can enjoy the natural landscapes or the curated flora at the Berkshire Botanical Garden, along with performances from the Berkshire Theatre Group.
08. Oak Bluffs
Relax on the sands of Oak Bluffs, located on Martha’s Vineyard, known for Joseph Sylvia State Beach, a two-mile stretch featured in “Jaws.” The town also attracts high-profile visitors, including the Obamas.
09. Nantucket
Finish your journey by visiting Nantucket, an isolated island that has a population of just over 11,000. History enthusiasts can discover three historic lighthouses—Great Point, Sankaty Head, and Brant Point—while enjoying seafood dining and boutique shopping.
10. Westford
Did you know skiing is possible in Massachusetts? Visit Westford, located near the New Hampshire border, to enjoy the Nashoba Valley Ski Area. This year-round destination also features hiking and biking trails, alongside attractions like The Butterfly Place, a vibrant indoor environment for various butterfly species.
