The 12 Most Charming Small Towns in Massachusetts

editor@purewow.com (PureWow)
·9 min read

As any student of American history already knows, the Commonwealth of Massachusetts was one of the O.G. states to join the union way back in 1788. It also gets props for being the first to write and adopt a constitution. While Boston has been the capital and main city since its founding, Beantown isn’t the only destination worth visiting. Massachusetts is teeming with small towns steeped in hundreds of years of history. Of course, you don’t have to be a scholar or have a penchant for the past to appreciate the enchanting communities scattered across the Bay State. After all, it packs a punch in terms of great food, shopping, beautiful beaches and seaside pursuits.

From places with Puritan roots and locales that served as battlefields during the Revolutionary War to a destination famous for witch hunts, these are the most charming small towns in Massachusetts.

RELATED: THE 15 MOST CHARMING SMALL TOWNS IN NEW ENGLAND

1. ROCKPORT, MA

Like a postcard come to life, Rockport is an endlessly photogenic—and dry (yes, that means no alcohol) seaside village with loads of characteristic New England charm and a population of 7,500 residents. This beloved summer getaway (which, we should mention, also wows in the fall, winter and spring) offers a blend of cute touristy and local stuff. Besides the galleries, gift shops and BYOB restaurants in the harbor area, go see Motif No. 1 (pictured above) and strike out on the waterside trails in Halibut Point State Park for splendid views that extend well into New Hampshire and Maine.

Where to stay:

2. PROVINCETOWN, MA

Perched at the northern tip of Cape Cod, Provincetown (P-town if you’re a local or frequent visitor) is a summer hotspot. The year-round population clocks in around 3,000, but that swells to 60,000 during peak season. Don’t let that deter you. This endearing seaside town has a rich history of progressiveness and inclusion that’s long lured artists, poets, entertainers and members of the LGBTQ+ community. Provincetown is famed for hosting epic Pride festivities, including its annual parade. While you’re there, def hit the galleries, nightclubs, restaurants, indie shops and beaches and grab a drink at A-House, the oldest gay bar in the United States.

Where to stay:

3. STOCKBRIDGE, MA

Perhaps you’ve heard of the Berkshires? The Western Massachusetts destination is a fixture on “The Real Housewives of New York City.” Though we can’t imagine anyone affiliated with this rural region wishes to be associated with the unseemly antics that go down at Dorinda's estate. Instead, the better connection is to Norman Rockwell. The American painter spent the last 25 years of his life deriving inspiration from Stockbridge. This pretty-as-a-picture town oozes charm and history with the backdrop of rolling hills. Obviously, you’re going to stop by the Norman Rockwell Museum. Be sure to check out Naumkeag, a botanical garden and Gilded Age mansion, too.

Where to stay:

4. CONCORD, MA

Concord is undeniably one of the prettiest small towns in New England and perhaps best known as the site of the first battle of the Revolutionary War. First up on your history crawl? Minuteman National Historic Park to hike, glimpse the North Bridge (pictured above) and enjoy a picnic lunch. You can also visit The Old Manse, where poet Ralph Waldo Emerson drafted his essay “Nature” in 1800, as well as Walden Pond, made famous by writer Henry David Thoreau and widely considered to be the birthplace of the American conservation movement. Cap things off with a trip to Louisa May Alcott's Orchard House.

Where to stay:

5. OAK BLUFFS, MA

The idyllic town of Oak Bluffs earns our vote as *the* place to stay on Martha’s Vineyard. With Ocean Park, Circuit Avenue and Joseph Sylvia State Beach—a two-mile stretch of soft sand and shallow water that served as a filming location for the 1975 flick Jaws—plus the oldest operating platform carousel in the country, you may never even make it to Edgartown. (Oh well, there’s always next time.) Guess that’s why everyone from the Obamas and the Clintons to celebrities like Spike Lee have escaped to this quintessential New England summer retreat.

Where to stay:

6. SALEM, MA

Salem, which is notorious for its 1692 witch trials in which more than 200 people were accused of practicing hocus pocus, casts a spell on all who visit. (Sorry, that was just wicked easy.) Not just a place to spend Halloween and learn about America’s most famous witch hunt, this coastal city that feels a lot like a town on the north coast of Massachusetts has a lot going for it that no one really talks about. So we will do a little bragging on behalf of the Essex Street Pedestrian Mall, scenic harbor cruises and the Peabody Essex Museum.

Where to stay:

7. LENOX, MA

Another small town that’s nestled in the Berkshires of Western Massachusetts, Lenox is a low-key cultural dynamo that’s surrounded by winsome scenery. Besides outdoorsy enticements such as Pleasant Valley Sanctuary, it’s brimming with fine dining restaurants (Table Six, The Portico by Jeffrey Thompson and Cafe Boulud receive rave reviews from patrons) and interesting attractions like The Mount, Edith Wharton's Home (pictured above). Lenox is also home to Shakespeare & Company (so it goes without saying that you’re going to see a play) as well as Tanglewood, the summer headquarters of the Boston Symphony Orchestra.

Where to stay:

8. CHATHAM, MA

If you’re a fan of sun-drenched beaches, look no further than Chatham. It boasts some of the most gorgeous coastal spots in all of Cape Cod (and that’s saying something), plus a quaint downtown. After catching some rays or going for a leisurely stroll, spend the afternoon browsing the cute shops and savoring seafood at top-notch restaurants like Impudent Oyster (we hear the bacon-wrapped scallops are delish). You’ll definitely want to carve out some time to visit the Monomoy National Wildlife Refuge, the Atwood Museum, the Shark Center and the Chatham Lighthouse.

Where to stay:

9. NANTUCKET, MA

Despite being a relatively small state, Massachusetts counts two of the most iconic East Coast summer beach getaways among its lengthy roster of must-visit destinations. We already discussed Martha’s Vineyard. Now it’s time to dive into the adorableness that is Nantucket. (For the sake of clarity, it’s worth mentioning that both the town and island share a name.) This legendary escape off the coast of Cape Cod attracts well-heeled holiday goers with its wind-swept dunes, cedar-shingled houses that belong on the cover of Architectural Digest and perfectly preppy atmosphere. Cobblestoned streets, upmarket boutiques, seafood eateries and historic churches are also part of the package.

Where to stay:

10. NEWBURYPORT, MA

When we think of adorable small towns in Massachusetts, Newburyport instantly springs to mind. Located 50 minutes from Boston, this coastal gem has a long history dating back to the Revolutionary War. Afterward, abolitionism gained popularity and it became an important stopping point on the Underground Railroad. All its appeal certainly isn’t in the past. Today, Newburyport flaunts a mix of modern and old-fashioned delights. Whale watching tours speak to its maritime roots. You’ll also find ice cream parlors, antique shops, scenic trails in Parker River National Wildlife Refuge and a lovely boardwalk.

Where to stay:

11. NORTHAMPTON, MA

A funky, crunchy, bohemian haven with tons of culture and strong left leanings, Northampton is a stomping ground for artists, authors, musicians, activists, students and academics. Much of the activity centers around Smith College, which has an art museum and a beautiful botanical garden. There’s also plenty of attractive architecture to admire, bookstores worth browsing, Thornes Marketplace, concerts at Academy of Music Theatre, the R. Michelson Galleries and everything from pedal boating to mini-golf in Frank Newhall Look Memorial Park. While cycling enthusiasts can bike the Norwottuck Rail Trail.

Where to stay:

12. IPSWICH, MA

Ipswich might just be the most underrated destination on our list. You’d think a place that’s packed with New England traditions and charm would be a bonafide tourism darling. To be clear, it’s not like Ipswich is some best-kept secret. But coastal towns like Rockport and Newburyport certainly get top billing. What the masses don’t know is their loss and your gain. Because it means more space to sprawl out on Crane Beach, fewer tourists at Castle Hill on the Crane Estate, shorter waits at restaurants and the chance to explore Sandy Point State Reservation sans crowds.

Where to stay:

RELATED: THE 15 BEST TOWNS IN VERMONT THAT WE MIGHT JUST MOVE TO

PureWow may receive a portion of sales from products purchased from this article, which was created independently from PureWow's editorial and sales departments.