9 Massachusetts Towns That Locals Love
Massachusetts, nicknamed "the Bay State," is known for historic cities, well-known attractions, and local communities that draw people in each year. These communities each have something that makes them distinct, whether it is access to natural areas, a piece of Colonial-era history, annual events that mark the calendar, or a community atmosphere that is welcoming during the summer. The state gives visitors a range of towns that residents value and call home.
Newburyport
Newburyport is a coastal city on the Merrimack River in the northeastern part of the state, known for its maritime heritage. To learn more about the city's maritime past, the Custom House Maritime Museum is a central stop, as the building was once the United States Custom House and highlights shipbuilding from the 18th and 19th centuries. Other exhibits in the museum cover the history of the U.S. Coast Guard and display historic artifacts. On the eastern side of town is Plum Island Beach, where people can take in views of the Atlantic Ocean, walk the shoreline, go fishing or kayaking, and visit nearby restaurants.
During the spring and fall, the Newburyport Artwalk allows residents and visitors to visit the art galleries in the community and see the work local artists create, including paintings, jewelry, ceramics, and photography. The tour takes place in the city's Historic District, which includes the Blochaus Art Gallery, the Threadneedle Gallery of Fine Art, and the Gallery on Federal, as each gallery presents art created by local artists for the community to see.
Lexington
One of the most historic towns in the state, and in the country, is Lexington, which had a significant role at the start of the Revolutionary War, as the first shot of the war was fired in the town in 1775. The Lexington Battle Green is a historical monument marking where the first shot occurred, with a statue displayed in the park that is open year-round. Further down Massachusetts Avenue is downtown, where people can visit local restaurants, parks, and shops, such as Mario's Italian Restaurant for a quiet Italian dinner, and Emery Park in the center of town, which hosts community events and is a calm place to spend time on a sunny day.
An annual event held every April is Patriots' Day, a tribute to the minutemen who fought against the British on April 19, 1775, when the town hosts a parade and a reenactment of the battle that took place that spring day. The Lexington Lions Club also holds an annual Five Mile Road Race to commemorate the battle and give runners a way to begin the day with a challenging course.
Concord
Just like Lexington, the town of Concord also played a significant role during the beginning of the Revolutionary War and has had other historical importance over the centuries. Similar to the Lexington Battle Green, the Old North Bridge is an important landmark where about 90 British troops were sent to confront the Colonial Militia, but were outnumbered and eventually retreated to Boston after only partially succeeding in seizing and destroying military supplies. Downtown has a long history, with the Concord's Colonial Inn in the center of town, where guests can stay in rooms dating back to 1716, along with modern amenities.
A local event in town honoring state and national history that takes place in May is Paul Revere's Bike Ride, where residents and visitors can take part in a recreational bike ride through the community and several nearby towns. Participants ride past historical landmarks and attend a post-ride gathering on the Concord Museum lawn at the end of the route.
Lenox
Near the state border with New York in the Berkshires is the town of Lenox. Downtown is a welcoming place for visitors to spend time and see the local spirit of the community. The Black Squirrel Cottage is a bed and breakfast next to downtown, where people can stay up to two nights in the small cottage. Further down Walker Street is the American Craftsman Gallery, where visitors can view and purchase handmade pieces, including wood, glass, and home decor.
At the beginning of September is the Lenox Jazz Stroll, an annual jazz festival with family-friendly performances in Lilac Park, held over two days depending on the schedule. Locals and visitors can sit and listen to jazz performances from local and national artists.
Falmouth
On the southwestern end of Cape Cod is the coastal town of Falmouth, a community known for its beaches that visitors and residents use throughout the year. On the shoreline is the Falmouth Tides Hotel, where guests have access to the Tides Private Beach, views of the Vineyard Sound from their suites, fresh coffee from Little Blue, and convenient access to ferries, yacht clubs, and marinas that travel to Martha's Vineyard. Falmouth Heights Beach allows residents and visitors to spend time in the sun, hear the waves, and visit the Shipwrecked Restaurant across the beach for a meal.
An annual event to take part in is the Falmouth Road Race, a seven-mile race that has brought runners, Olympians, and athletes to the town since August 1973. Runners pass by the beaches and have views of the ocean and landmarks, such as the Nobska Lighthouse after the first mile, and the race concludes by Falmouth Heights Beach.
Chatham
At the eastern end of Cape Cod, about 40 to 50 miles east of Falmouth, is the beach town of Chatham. The Chatham Fish Pier Viewing Dock is a place where people can fish, observe the fishing activity in the community, watch seals in the water, and take in views of the cove and nearby islands. Just south of the dock is Chatham Lighthouse Beach, a quiet beach near the Coast Guard Station, the Chatham Beach and Tennis Club, and the Chatham Lighthouse. On the southern end of the beach is the Ship Skeleton off Cape Cod, which is a notable stop for visitors interested in local history.
An annual alcohol free event held in town to welcome the New Year is First Night Chatham. The event takes place every New Year's Eve and begins with a town photo in front of the Chatham Lighthouse at 12:00 p.m. ET. It then features performances by local artists, family-friendly activities, and fireworks to mark the start of the New Year.
Stockbridge
About six to seven miles south of Lenox is the historic Berkshires town of Stockbridge. In the center of downtown is the Red Lion Inn, a hotel that has been open since 1773, with suites that blend historical elements and modern amenities, and the Lion's Den bar, which serves food, craft drinks, including zero-proof cocktails, and hosts live music. Just north of downtown is the Berkshire Botanical Garden, one of the oldest public gardens in the country, with 24 acres of flower beds, more than 3,000 plant species, and a water garden pond. The gardens also host private events such as weddings, which create a memorable setting for guests.
In mid-August, the annual Stockbridge Summer Arts and Craft Show takes place, where artists from across the region set up along Main Street to sell handmade work, including paintings, ceramics, jewelry, glassware, vases, and more. Admission is free, and residents and visitors can see the art and spend time in the local restaurants, cafes, hotels, and shops, such as the Main Street Cafe for a cup of local coffee and the Lost Lamb for pastries and pies.
Pittsfield
Just north of Lenox is Pittsfield, the largest city in the Berkshires, known for its cultural scene. In the center of downtown is Park Square, a 1.5-acre park surrounded by local businesses, shops, and restaurants, with a Civil War memorial and space for community events. A spot to get a drink downtown is Patrick's Pub, which serves food and drinks, including cocktails, wine, and craft beer. The Berkshire Museum is also close by, giving visitors a way to learn more about the region's history through its exhibits and events.
A local event that keeps the night active and centered on music is the Pittsfield City Jazz Festival. The festival takes place from April to May for Jazz Appreciation Month, beginning with Jazz About Town, where local musicians perform in restaurants and venues across the city. Other parts of the festival include Jazz Brunches and Jazz Prodigy Concerts, which maintain the presence of jazz throughout the community.
Tisbury
On the northern tip of Martha's Vineyard is the coastal town of Tisbury, home to the village of Vineyard Haven. A summer spot to visit in town is Owen Park Beach, where visitors and residents have calm ocean waters, a playground for families, and a dock for boats and people who want to spend time on the water. Downtown has a range of local restaurants, hotels, and shops, including the Vineyard Harbor Motel, which gives guests access to a private beach and is within walking distance of activity in town. Across the street is ArtCliff Diner, where patrons can order warm food in a classic diner setting.
The annual Tisbury Street Fair that occurs every July is a way to see the community. The event marks the founding of the town with food vendors serving items such as lobster rolls and cotton candy. Visitors can also shop at local stores, view local craft art and paintings, listen to live music, and take part in various other activities.
Why These Communities Stand Out
When it comes to these communities in Massachusetts, they give visitors from larger cities and out of state a mix of history, landmarks, and coastal settings in Cape Cod and Martha's Vineyard. The events held throughout the year add to the character of each place and reflect the people who live there. A weekend trip or a short vacation in the New England region can give travelers a change of pace and a clear sense of what makes these towns steady parts of local life.
