11 Best Small Towns to Visit in Massachusetts

Massachusetts makes small-town travel easy: coastal harbors on the North Shore, artsy villages in the Berkshires, classic Cape Cod communities, and ferry-friendly islands just offshore. Some places are all about early American history (think battlefields, old meetinghouses, and historic town centers), while others lean into beach days, seafood shacks, galleries, and waterfront strolls.

This list highlights a mix of styles and regions across the state. You’ll find walkable historic towns like Concord, where you can pair a scenic downtown with stops tied to the American Revolution. And if you’re craving a true getaway, island towns like Edgartown and Nantucket add ferry rides, lighthouses, and slower-paced days by the water. Below are some of the best small towns to visit in Massachusetts.

Concord

In 1775, tensions in Massachusetts were running high. About 700 British soldiers marched to Concord to seize colonial weapons and ammunition. Local militias got word and weren’t willing to back down. Historians still debate who fired the first shot at the Battles of Lexington and Concord, but the impact is clear: the fighting helped ignite the American Revolution. For history buffs, Concord is a must-see—and it’s also a beautiful town to explore on foot. To get the full story, set aside several hours (or a full day) for Minute Man National Historical Park, located in and around town.

Provincetown

Even if you’ve never been to Provincetown, you’ve probably heard of it. The Pilgrims aboard the Mayflower first landed in Provincetown Harbor before continuing on to Plymouth, giving the town a notable place in early American history. Today, at the tip of Cape Cod, Provincetown is a classic resort town and a favorite summer getaway. With sandy beaches, a lively arts scene, and plenty of galleries—including the Rice Polak Gallery for contemporary art—it’s easily one of the best small towns to visit in Massachusetts.

Rockport

Rockport is about 43 miles from Boston—an easy drive of roughly an hour—yet it can feel a world away. Named for the area’s granite, Rockport is a laid-back coastal town known for its scenery near the northern tip of Cape Ann. A highlight is Bearskin Neck, a narrow strip lined with galleries, shops, and casual restaurants that leads toward the harbor. For a classic visit, grab coffee at Brothers Brew Coffee Shop, then head to Halibut Point State Park, a former granite quarry with walking trails and sweeping ocean views.

Stockbridge

Stockbridge is the definition of picturesque—tucked into the Berkshires of western Massachusetts. The town’s Main Street feels straight out of a postcard and is a pleasure to stroll, especially around the holidays. Artist Norman Rockwell, best known for his covers for The Saturday Evening Post, lived in Stockbridge for the last 25 years of his life. Today, the Norman Rockwell Museum holds an impressive collection of original works and memorabilia, and it remains one of the town’s top attractions.

Northampton

Northampton may not be as Revolutionary-era famous as Concord or Provincetown, but it still ranks among Massachusetts’ best small-town destinations. Home to about 28,900 residents, it hits a sweet spot between small-town charm and a lively downtown. With Smith College at its center, Northampton has a creative, college-town vibe and plenty to do beyond campus. For a great visit, check out the Smith College Museum of Art, browse Thornes Marketplace, or take a relaxing stroll through the Smith College Botanic Garden.

Wellfleet

The East Coast is one of the best places in the country for seafood, and Wellfleet is especially known for its oysters. Locals and experts often point to the waters of Cape Cod Bay—along with factors like salinity—as part of what gives Wellfleet oysters their reputation. To taste them for yourself, order a plate at Moby Dick’s (expect a wait in peak season). And if you’re here for the shoreline, Marconi Beach is close by—a popular stretch of sand backed by beautiful coastal scenery.

Williamstown

Williamstown is tucked into the northern corner of the Bay State, about 168 miles west of Boston. With around 4,500 residents, it has the small-town feel you’d expect, plus the mountain-and-forest scenery the Berkshires are known for. After exploring the compact center, visit the Williams College Museum of Art, widely regarded as one of the best college art museums in the country. Nearby, the Sterling and Francine Clark Art Institute (often called “The Clark”) is another highlight, with an outstanding collection that includes French Impressionist works.

Edgartown

One of Edgartown’s claims to fame is that it was the first colonial settlement on the island now called Martha's Vineyard. For history buffs, that alone makes it worth the trip. Today, Edgartown pairs that history with a walkable downtown and a peaceful waterfront, where you can admire classic seaside cottages—many with Greek Revival details, tidy porches, and well-kept gardens.

Nantucket

If you’re looking for rest, relaxation, and a toe-in-the-sand getaway, Nantucket is a strong pick. The town and island sit about 30 miles off Cape Cod and offer lighthouses, beaches with soft sand, and an easygoing pace that makes it simple to unplug. For a memorable meal with live music, Cisco Brewers (at 5 Bartlett Farm Road) is a popular stop.

Sandwich

Despite the name, Sandwich is one of Cape Cod’s oldest—and prettiest—towns. It sits at the eastern end of the Cape Cod Canal, just east of Bourne. Sandwich is often noted as the earliest European settlement on Cape Cod, a peninsula known for its shoreline, seafood, and long history.

Today, Sandwich is home to about 2,800 residents and features historical landmarks like the Hoxie House. For a deeper look at local heritage, stop by the Sandwich Glass Museum, which highlights the town’s glass-making past and often offers live glass-blowing demonstrations.

Chatham

Chatham sits on the “elbow” of Cape Cod and, with a population of about 1,500, is small—but packed with charm. With classic Cape Cod architecture and a relaxed pace, it’s an easy place to slow down for a weekend. Between the working Chatham Lighthouse, scenic drives past impressive homes, and a walkable town center, Chatham feels tailor-made for an idyllic coastal escape.

Other highlights include the Atwood Museum, which explores local history through exhibits and ship models, and the Shark Center, where visitors can learn more about sharks and local conservation efforts.

The Takeaway

New England’s shoreline is dotted with small towns, many of them among the most historic in the United States, and Massachusetts has some of the region’s best. From well-known stops like Concord and Provincetown to quieter getaways like Chatham and Sandwich, the Bay State makes it easy to plan a trip built around walkable downtowns, coastal scenery, and deep history. In other words, Massachusetts’ best small towns are not just standouts in New England—they’re among the best in the country.