The Best Small Towns in Massachusetts

The islands of Nantucket and Martha’s Vineyard are popular Massachusetts destinations, as they’re easily accessible by ferry from Cape Cod. And there are a few small towns within those that are particularly nice to visit – one of those is Edgartown on Martha’s Vineyard. Back in the 1800s, it was a prominent whaling port and still maintains much of the charm it had then. The charming downtown is filled with boutiques, art galleries, and restaurants, including the Seafood Shanty, Alchemy, and Vineyard Scoops (a must for ice cream). No matter what part of the island you’re staying on, make sure you have a bike on hand, as that can be a nice—and convenient—way to get to the local beaches and town. Also, be sure to check out Oak Bluffs and Vineyard Haven if you find yourself on Martha’s Vineyard.

Marblehead is a picturesque, quaint waterfront town just 16 miles north of Boston, with mostly bed and breakfast options for overnight accommodations. If you’re looking for more of a boutique hotel vibe, opt for The Hotel Marblehead, which still upholds the town’s history while giving you modern amenities at the 14-room hotel. Of course, when visiting a place like Marblehead, you’ll want to check out one of the local beaches—in this case, Devereaux and Preston Beaches are ideal options. For dining out, check out the 5 Corners Kitchen, Casa Mia, Little Harbor Lobster Company, or the Three Cod Tavern.

In northern Massachusetts, not very far from the Southern New Hampshire border, is another coastal town, Newburyport. This historic town dates back to 1635—though today it is mostly visited for its waterfront restaurants and a quaint downtown area filled with local boutiques and other shops. If you’re in the area during the warm weather months, take a drive over to Plum Island and spend the day at the beach or walking around the Sandy Point State Reservation.

You can’t go wrong with any of the small towns that make up Cape Cod, but if you head all of the ways to the tip of the peninsula, you’ll wind up in Provincetown, known to locals as “P-Town.” The town is known for its gay culture and art galleries, and it’s also home to great restaurants, shops, and beautiful beaches and lighthouses along the Cape Cod National Seashore. Their annual Pride festival is called Provincetown Carnival and brings in lots of crowds and festivities.

It’s also worth noting that Provincetown is quite dog-friendly, with resorts like the Surfside Inn allowing four-legged friends to stay overnight. P-Town is accessible, of course, by driving, but also by a ferry that leaves from Boston. 

Salem is known as home to the Salem Witch Trials and is a big place to visit during Halloween season, as this is the time of year when the annual Salem Haunted Happenings takes place with lots to do for the whole family. More recently, Salem has also introduced the Holiday Happenings festival from late-November to the start of the New Year. But no matter what time of year it is, you can take a variety of spooky tours or explore on your own and learn all about the history of this town. And when choosing where to stay, check out the historic Hawthorne Hotel or The Hotel Salem, a Lark Hotels property.

If you’re looking for a small beach town less than an hour from the city (give or take with traffic, depending on the time of year!) head to Scituate, located on Massachusetts’ South Shore. Here, you’ll find beautiful beaches—Humarock, Minot, and Peggotty, to name a few—along with several waterfront restaurants, including Riva Restaurant & Bar, Oro, and the Lucky Finn Café.

There aren’t many places to stay in Scituate—but that might just be part of its beauty as it doesn’t have a tourist vibe to it. If renting a house isn’t your thing, try The Inn at Scituate Harbor or head over one town to the Cohasset Harbor Resort or the Red Lion Inn. During the summer months, all forms of lodging will book up early, so plan accordingly, especially if you are in town for an event over a specific weekend.

If you want a taste of the South Shore by staying a bit closer to the city, Hingham is another option. 

Stockbridge is one of many towns to visit in Massachusetts’ Berkshires, located west of the city of Boston. Here you’ll find all sorts of activities, from music festivals and art galleries, to historic homes and trains perfect for hiking, cycling, snowshoeing and more.

This area is beautiful at any time of year, but it’s particularly special during fall foliage season as the leaves change color and create picture-perfect scenes everywhere you look. Stockbridge is home to the Norman Rockwell Museum, which houses his work, and another special place to visit is the Berkshire Botanical Garden.

For accommodations, there are plenty of inns and bed and breakfasts, along with more luxurious options like the Cranwell Resort or the Canyon Ranch Lenox, the latter of which is actually just outside of Stockbridge about 10 minutes away.