Massachusetts's 7 Most Laid-Back Towns For 2025

Home to over 1,500 miles of shoreline, some of the country’s oldest art colonies, and prolific mountains like the Berkshires, Massachusetts has plenty of spots where travelers can kick back and truly relax. Perhaps unsurprisingly, some of the best places to experience this relaxation are in the state’s small towns. If your idea of a stress-free weekend involves gallery hopping, an afternoon of fishing, or a short mountain hike, the following seven municipalities should be on your radar.

Provincetown

Provincetown, resting at the farthest tip of Cape Cod, is one of the country’s oldest continuous art colonies and a popular beach destination. The town is the perfect gateway to explore Cape Cod National Seashore Park, with beaches like Herring Cove and Race Point Beach serving as access points to explore it.

Travelers interested in discovering the town’s historic art scene can do so at places such as the Provincetown Art Association and Museum, which has been operating for over a century and boasts a permanent collection of more than 3,000 works. Hoping to buy a piece of your own? Many of the town’s galleries are concentrated in East End and Commercial Street, with Commercial Street alone featuring over 40 galleries to explore.

Oak Bluffs

Oak Bluffs, a well-known town on Martha’s Vineyard, offers all kinds of relaxing activities, including unwinding at a waterfront park, embarking on a fishing charter, and exploring the town’s architecture. Ocean Park is one of the town’s central landmarks, covering seven grassy acres near the ferry exit, perfect for an afternoon picnic.

If you are hoping to spend a few hours on the water, consider reserving an excursion with Skipper Fishing Charters, which has been voted as the Vineyard’s best fishing charter for more than 20 years. A few of the fish you might be able to catch during your relaxing afternoon out include black sea bass, scup, fluke, and tautog. As you stroll down the town’s streets, you will likely encounter the Gingerbread Cottages, a cluster of peculiar homes dating back to the late 19th century that have become a regional icon.

Stockbridge

Located in the beautiful Berkshire County, Stockbridge is filled with adorable cottages, gardens, and inns to explore. In fact, the Berkshire Botanical Garden, established in 1934, is one of the oldest in New England. Today, these gardens cover 24 acres and feature dozens of unique garden spaces, making it easy to spend an afternoon here.

Art lovers will also want to stop by Chesterwood, the summer home and studio of renowned sculptor Daniel Chester French. Many of the painter's works continue to be on display at the cottage property today. At the end of the day, travelers can relax at the Red Lion Inn, welcoming guests since 1773, with four unique lodging options: The Main Inn, Village Houses, Maple Glen, and the Norman Rockwell Firehouse.

Rockport

Rockport continues the artistic tradition found in many of Massachusetts’ towns, famously home to one of the most painted structures in the United States. Although the original was destroyed in a 1978 blizzard, you can still see its iconic replica along the town’s Bradley Wharf: the red fishing shack known as Motif No. 1.

Visitors can continue their relaxed afternoon by heading over to the Rockport Art Association & Museum, which houses more than a century’s worth of artwork from across Cape Ann. It also hosts a variety of special exhibitions throughout the year, so be sure to check the calendar before planning your visit. To experience a bit of the town’s maritime culture, consider booking a tour with Rockport SeaVenture, which provides lobster catching, sightseeing, and wildlife tours on the Rockport Harbor.

Great Barrington

In Great Barrington, you can kick off the day with a leisurely hike and wrap it up with a night in town, perhaps with a craft beer or a night at the theater. If hiking is something on your radar, you will definitely want to add Monument Mountain to your itinerary. Three trails wind along this 1,642-foot peak, each of which offers views that look out over Mount Greylock and the Catskill Mountains.

If it is a local craft beer you are seeking, make sure to stop by the Big Elm Great Barrington Taproom, which has flights, 10-ounce pours, and pints available to sample. The Mahaiwe Performing Arts Center, meanwhile, has an excellent calendar of events worth browsing, including live music performances, lectures, and special holiday shows.

Shelburne Falls

Shelburne Falls is famous for its gorgeous Bridge of Flowers, which was just recently reopened after an extensive, multi-million-dollar renovation project. Once part of the Colrain Shelburne Railroad, this bridge was transformed in the early 20th century by the Shelburne Falls Women’s Club into a flourishing flower bridge, now blooming from April through October with trees, perennials, annuals, shrubs, and vines.

Travelers can also ride the trolley that once crossed the bridge at the Shelburne Falls Trolley Museum, which offers both trolley rides and old-fashioned pump car rides. If geology and rock formations intrigue you, you’ll enjoy a visit to the town’s “glacial” potholes on Deerfield Avenue, which date back roughly 14,000 years and vary from six inches to 39 feet across.

Swampscott

Founded in the 17th century as a fishing village, Swampscott is now a peaceful coastal town that continues to preserve its fishing heritage. The city is home to one of the oldest operating fish houses in the country: The Swampscott Fish House, which dates back to 1896. Its pier is also a great place to appreciate views of the Massachusetts Bay and Boston skyline.

Locals and visitors are also frequently found at Beach Bluff Park, which sits along the oceanfront and is home to the Sun Circle installation, benches, and winding paths. Travelers looking for a bite to eat can swing by the Dockside Pub, which serves dishes like clam chowder, fried scallops, fish and chips, and many other favorites from the sea.

If you live in Massachusetts, you do not need to hop on a plane to enjoy some rest. There are so many destinations within your own state, often just a short drive away, that will offer you that same laid-back atmosphere you are craving! While some towns, like Oak Bluffs and Provincetown, focus on the coast, other destinations, such as Great Barrington and Stockbridge, are ideal for exploring the tranquility of the Berkshires. Regardless of the kind of relaxation you are seeking, rest assured that you are about to experience the most peaceful side of The Bay State!