10 Best Small Towns In Massachusetts For A Crowd-Free Summer
The Commonwealth of Massachusetts, also known as "the Bay State," is full of natural wonders and exciting towns and cities to explore. Each community has its own unique charm that attracts visitors from New England and across the United States, especially during the summer months when everyone wants to go to the beach and escape the concrete jungle in major cities. From waterfalls to wineries and everything in between, these 10 small towns in Massachusetts have everything your heart could possibly desire for a crowd-free vacation this summer.
Rockport
Rockport is a charming seaside town in Essex County known for its access to the ocean, vibrant arts community, and scenic, walkable downtown. Being a seaside community, Front Beach is an excellent starting point for your visit. It's an active beach on Sandy Bay and an easy walk from the town itself, as well as the hotels and inns for visitors looking for a relaxing weekend getaway. Front Beach may be small, but it's a very relaxing place to unwind and refresh during a lazy summer day in New England.
Once you have had your fill of the beach, the town of Rockport is a great place to explore with all kinds of local shops, hotels, and restaurants. Bearskin Neck is a wharf within downtown that also gives visitors and residents access to a scenic overlook of Sandy Bay. A must-visit on Bearskin Neck is My Place By The Sea, an award-winning restaurant featuring fresh seafood and outdoor seating with incredible views.
Stockbridge
Stockbridge, a relaxing town in the Berkshires, has much to offer, including a bit of American pop culture. Beloved artist, Norman Rockwell, was a resident of Stockbridge and the surrounding landscape inspired much of his work. The Norman Rockwell Museum is located within the community and is dedicated to showcasing Rockwell's work, as well as his cultural impact and legacy.
Another historic and exciting place to visit in town is the Red Lion Inn, which opened its doors in 1773 as a tavern and has become a very popular summer hotel in the Berkshires. Within the historic hotel is The Lion's Den, which offers local bites, drinks, and live music for an unforgettable summer night. Stockbridge is a natural beauty with plenty of activities to enjoy in the outdoors. Olivia's Overlook is a favourite spot for incredible views of the area, and if you're up for a bit of a hike, the Charcoal Trail is a great option for exploring the Yokun Ridge. The 1.7-mile loop is considered to be a moderately challenging route with plenty of opportunities for scenic photo ops along the way.
Lenox
Just seven miles north of Stockbridge is the Berkshires town of Lenox, a small community of just over 5,000 people. Like many of these sweet spots, Lenox is known for its vibrant arts, culture, and theater scene, historical attractions, and natural beauty. Shakespeare & Company presents a range of plays and events throughout the summer, including, of course, Shakespeare classics. They host performances in a handful of spaces, including a garden theater, an indoor playhouse, and the open-air Arthur S. Waldstein Amphitheater.
Lenox also has plenty of art galleries thriving in the community, such as the Wit Gallery, which showcases a diverse collection of art from experienced and emerging artists. During the summer, the Tanglewood Music Festival takes place on the Tanglewood Estate, featuring the Boston Symphony Orchestra, along with jazz, pop, and contemporary music.
Great Barrington
Great Barrington is just south of Lenox, with its charming downtown, cultural attractions, and gorgeous natural surroundings in the Berkshire Mountains. The Bernay Fine Art Gallery offers works from local artists, while the rest of downtown is filled with locally-owned businesses and restaurants. Great Barrington is very walkable with a great display of old and historic buildings along Main Street.
Lake Mansfield Beach and Conservation Forest Trails is a small, relaxing beach on a lake owned and maintained by the community. Lifeguards are on duty from May until August, making this a popular swim spot for locals and visitors alike. There are also trails in the adjacent 29 acres of woodland, and they are dog-friendly, though the beach area itself is closed to pets. The lake features a boat launch as well, for those who wish to get out on the water to fish or paddle.
Sandwich
On lovely Cape Cod, Sandwich is a town with a population of around 20,000 people and is known as the oldest in the region, having been settled in 1637 and incorporated in 1639. Sandwich is also one of the quieter Cape Cod towns. There is a boardwalk giving locals and visitors access to Town Neck beach, a pleasant and popular place for a stroll along the sandy shoreline. Not too far from the beaches is the Sandwich Marina, where people who rent or own boats can explore Cape Cod Bay. The marina is open seven days a week and offers plenty of amenities, and there are several restaurants nearby for a nice meal before or after a day on the water. The Pilot House and Fisherman's View are both local favourites.
Further inland, the town has a charming and interesting history as well, which can be explored with a trip to the Dexter Grist Mill, a historic mill that's now a museum showcasing what life was like in the 17th century. The museum also sells freshly ground cornmeal in old cloth flour bags for all who visit. Another exciting museum to visit in town is the Sandwich Glass Museum, which shares the history of glassmaking and the artists who continue to hone their craft.
Truro
Truro is a coastal town flanked by beaches on either side. Corn Hill Beach is easily accessible with calmer waters and breathtaking sunsets, while Longnook Beach is a bit more secluded with towering dunes and panoramic ocean views. Another coastal treasure is the Highland Lighthouse. The first lighthouse on Cape Cod was established in 1797, but the current tower was erected in 1857, replacing the original towers built in 1797 and 1831. The lighthouse is open daily from May through October, with 69 steps leading to the top where your efforts will be rewarded with stunning Cape views.
Truro Vineyards of Cape Cod is a family-owned winery offering the Cape Cod region handcrafted wines and spirits in their tasting room, as well as a gift shop and food truck dining. They also host a range of community events and live music, including Sunday Funday all summer long, featuring a DJ and ice cream truck.
Orleans
Just south of Truro is Orleans, a coastal town with a population of around 6,000 residents. Naturally, Orleans has its fair share of beautiful beaches, as well as a lively arts scene, and a strong sense of community. Collins Galleries calls Orleans home, with its boutique-style approach to showcasing and celebrating fine art, and the Academy Playhouse presents a range of theatrical productions by local talent for all to enjoy.
Similar to Truro, Orleans also has two beautiful beaches on each side of town: Skaket Beach and Nauset Beach. Skaket Beach has shallow waters and tidal flats to its proximity to Cape Cod Bay, making it perfect for exploring the beach on foot. It is also west facing for spectacular sunset views. Nauset Beach, on the other hand, is right on the ocean and famed for its dramatic sand dunes and wide beach. This is the more lively of the two options, with food trucks and 10 miles of wild summer surf.
Cheshire
Cheshire is perhaps best known for giving 1,235 lbs. of Mammoth Cheese to President Thomas Jefferson in 1802, crafted from the milk of every cow in town. Jefferson paid $200 for it, per his custom of refusing gifts, but the story remains a treasured piece of Cheshire lore and is a testament to the town's generous and entrepreneurial spirit. Today, there is a concrete cast of the block of cheese in the center of town with a plaque dedicated to John Leland, the man behind the political gesture.
On the edge of town is the Jones Nose Trail, a short, steep trail that offers access to the Appalachian Trail and Mount Greylock. Round Rocks Trail, on the other hand, is perfect for family hikes with two scenic viewpoints along the way. The Harbour House Inn is a charming bed and breakfast in the heart of the Berkshires perfect for weddings, vow renewals, family reunions, or a weekend with friends.
Mount Washington
Not far from Great Barrington is the Berkshire town of Mount Washington, known as "the Town Among the Clouds," due to its elevation and frequent cloud coverage, and named in honor of George Washington during the Revolutionary War. In the northwest corner of town is Bash Bish Falls State Park, home to the tallest single-drop waterfall in the Commonwealth at 60 feet. The trail to the falls is a relatively easy out and back route that takes about an hour to complete.
The town is surrounded by nature, namely the Mount Washington State Forest, which spans several thousand acres filled with red oaks, over 30 miles of trails to explore, and panoramic views for days. Race Brook Lodge, about 20 minutes from town, is a rustic retreat that offers live music, workshops, and unique guest rooms, as well as a swimming pool, sauna, and organic farm.
Wellfleet
The coastal town of Wellfleet boasts a sweet location along the Cape Cod National Seashore, which was established in 1961 by President John F. Kennedy and preserves over 40 miles of beautiful coastal shoreline in the state, protecting natural habitats, unspoiled beaches, dunes, salt marshes, and woodlands for residents and visitors to enjoy. Just like Truro and Orleans, Wellfleet is bordered by two stretches of beach, which include Cahoon Hollow Beach and Mayo Beach. Cahoon Hollow is a popular spot known for its dramatic 75-foot dunes, soft white sand, and the Beachcomber, a restaurant with outdoor seating and excellent views of the ocean.
Wellfleet Preservation Hall is an arts and cultural center which hosts rotating exhibits and community events. On the west side of Route 6 is the Wellfleet Bay Wildlife Sanctuary, a nature reserve established by the Massachusetts Audubon Society, that provides a safe haven for many species of local flora and fauna and is a great spot for birdwatching and wildlife viewing.
Each of these communities boasts a connection to nature, whether it's in the Berkshire Mountains or right on Cape Cod. These towns have their own unique personalities, vibrant cultures, and rich histories set against the coastal landscapes and forested foothills of Massachusetts. Whether you are looking to take a hike or a long walk on the beach, these 10 small towns are guaranteed to get you off the beaten track and into a world of your own this summer.
