10 Of The Friendliest Little Towns In Massachusetts
As one of the oldest states in the US, Massachusetts is home to some of the country’s oldest communities. Many towns date back to the 17th and 18th centuries, home to families who have lived there for generations. These small towns celebrate their heritage through summer arts festivals, concert series, weekly farmers markets, and long-standing family-owned seafood restaurants. Whether you are a Massachusetts local or simply planning a visit to the Bay State, you will quickly find that these ten small towns are among the friendliest.
Stockbridge
Stockbridge has a lively art scene, home to summer festivals and well-known artists. One of the most renowned festivals in Stockbridge is the annual Summer Arts & Craft Show, in which 30 jury-selected artisans and artists fill the historic district with their homemade crafts and artwork. Visitors should also make sure to visit Chesterwood, which is the studio, summer home, and gardens of the famed sculptor Daniel Chester French. After perusing the town’s art scene, consider grabbing a bite at one of Stockbridge’s local restaurants, such as Main Street Cafe, a breakfast and lunch spot that serves American classics like eggs benedict, omelets, and pancakes.
Rockport
Travelers looking to relax along the calming coast of Massachusetts will love Rockport. Two of the town’s beaches are easily accessible from downtown Rockport: Front Beach and Back Beach, both of which offer visitors the chance to sunbathe and swim. There are also several lighthouses to check out in Rockport, such as Straitsmouth Island Light. This lighthouse, listed on the National Register of Historic Places, dates back to the mid-19th century. The island where the lighthouse is located has been welcoming visitors since 2019, giving you the chance to see it up close. Throughout the year, Rockport has an impressive calendar of community events. If you enjoy live music, consider visiting the town in August during the annual Acoustic Music Festival, a free event that features a lineup of acoustic musicians.
Williamstown
Williamstown is another wonderful town to visit if you want to explore the fine arts scene of Massachusetts. The Clark Art Institute is an excellent starting place, offering both permanent collections and rotating exhibits. The museum's rotating exhibits currently include works by Mariel Capanna and a pastoral landscape exhibition. Those visiting in the summer must make sure to include the Williamstown Theater Festival in their itinerary, which celebrates everything from classic American plays to choreography on ice and chamber opera. Visitors can conclude their day with a memorable dinner at The Barn, a cozy yet upscale restaurant that supports the agricultural community by using locally sourced ingredients.
Deerfield
Deerfield is famously known for its location near Yankee Candle’s flagship store, the Yankee Candle Village. Here, Visitors can create their own candles, enjoy seasonal events, and browse the Yankee Candy Store, which offers over 125 types of candy! Make sure to check out the candle village during Christmas, as they deck it out with a Bavarian Christmas Village and Nutcracker Castle! Just a four-minute drive south of Deerfield, travelers will also reach the Magic Wings Butterfly Conservatory, which is home to approximately 4,000 domestic and exotic butterflies. Travelers looking for a particularly memorable night away will love the Deerfield Inn, which has been welcoming guests since its opening in 1884.
Great Barrington
Great Barrington is a tight-knit community in southwestern Massachusetts that is known for its farmers' markets, art galleries, and swimming holes. From May through November, travelers can stop by the weekly farmers market on Saturday, which offers everything from fresh produce to snow cones, coffee, and honey. To check out some of the local artists, travelers can visit galleries such as Bernay Fine Art, which features the work of artists who specialize in painting, photography, sculpture, glass, ceramics, and other mediums. For a day outdoors, visitors can head over to Lake Mansfield Recreation Area, home to a 29-acre pond and 29-acre conservation forest with places to swim and hike.
Provincetown
Located on the northernmost tip of Cape Cod, Provincetown is a laid-back coastal community home to the country’s oldest continuous art colony. There are all kinds of arts events put on throughout the year, including the 24-Hour Play Festival, in which playwrights, directors, and actors have just one day to prepare a show. The Fine Arts Work Center is another cultural landmark, home to the Hudson D. Walker Gallery, which highlights exhibitions from fellows. If you prefer to relax on the beach, consider heading to Herring Cove Beach, which is famous for its gorgeous Atlantic sunsets.
Shelburne Falls
It is hard for residents not to be friendly in Shelburne Falls, a beautiful riverside town in the Berkshire Foothills. In July each year, the town springs to life for the Shelburne Falls Porch Music Festival & Art Walk. During this festival, local musicians perform on the porches of homes across the town, showcasing the area’s jazz, folk, rock, classical music, and more. Shelburne Falls’ Bridge of Flowers is another beloved attraction to visit. Dating back to the early 20th century, travelers today can walk across this bridge in the springtime to appreciate flowering trees, shrubs, annuals, perennials, vines, and bulbs in color. While strolling throughout town, visitors should also keep their eye out for its mosaic murals, which were created by local artist Cynthia Fisher. There are nine to see!
Oak Bluffs
Oaks Bluffs is a friendly resort community on the northeastern shores of Martha’s Vineyard. There are plenty of delicious seafood restaurants along the town’s harbor, such as Nancy’s Restaurant, a family-owned seafood restaurant that has been operating in Oak Bluffs since 1960, open seasonally. Those looking to spend an afternoon fishing can book a local charter, with companies like Skipper Fishing Charters offering both daily fishing trips and sunset excursions. To ring in the summer season each year, Oak Bluffs hosts its annual Harborfest, which features live music, art, crafts, local food, and lots of vendors.
Adams
As an active outdoor community in Berkshire County, Adams offers residents endless opportunities to enjoy the sunshine and stay active. Mount Greylock, the state’s highest peak, is just a half hour’s drive away, home to 12,500 acres of preserved land and old-growth forests. Visitors can also enjoy the beautiful countryside aboard the Berkshire Scenic Railway, which departs from Adams and travels through the Hoosac Valley. One of the town’s most iconic events is its annual Thunderfest, which has been taking place since 2012 and features a festival of music, wine, beer, food, and lots of entertainment.
Lenox
Lenox is a historic and creative community that has beautifully preserved its artistic heritage. One of the town’s highlights is The Mount, a historic home where famous writer Edith Wharton once resided. Visitors can explore The Mount’s grounds, gardens, museum, and cultural center, immersing themselves in the writer’s life. Another interesting piece of history in town is Ventfort Hall, a 28,000-square-foot cottage that dates back to 1893, open year-round for tours daily. As the weather warms, Lenox celebrates its local music scene with the annual “Concerts in the Park” series, inviting visitors to bring a picnic, lawn chairs, family, and friends for a local concert every Wednesday evening from late June through late August.
Final Thoughts
If you are looking to explore the warmest side of Massachusetts this year, you’ll find that these 10 towns are a good place to start. Not only do they offer fun arts, music, and cultural festivals throughout the year, but they also are filled with beloved restaurants and historic landmarks that wonderfully preserve the heritage of the area. So step away from the large cities this year and get ready to experience the small-town spirit and hospitality of these friendly towns!
