Berkshire County Towns Make The List Of Most Charming Small Towns.

Berkshire County Towns Make The List Of Most Charming Small Towns. There is a new list out that has the top 12 most charming small towns and two of the towns here in the Berkshires cracked the top ten.

Coming in at number one is,

Offering up a blend of cute touristy and local stuff.


Besides the galleries, gift shops, and BYOB restaurants in the harbor area.

Perched at the northern tip of Cape Cod, Provincetown (P-town if you’re a local or frequent visitor) is a summer hotspot. It has long lured artists, poets, entertainers, and members of the LGBTQ+ community.


It is also known 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.

Coming in at number 3 is our very own STOCKBRIDGE
Stockbridge is a fixture on “The Real Housewives of New York City.” Instead, the better connection is to Norman Rockwell. The American painter spent the last 25 years of his life getting his inspiration from Stockbridge.


Also be sure to check out Naumkeag, a botanical garden, and Gilded Age mansion, too.

Concord is one of the prettiest small towns in New England and perhaps best known as the site of the first battle of the Revolutionary War.

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First up on your history crawl? Minuteman National Historic Park to hike, glimpse the North Bridge (pictured above) and enjoy a picnic lunch.

Oak Bluffs earns our vote as *the* place to stay on Martha’s Vineyard.

Oak Bluffs/Facebook
Oak Bluffs/Facebook

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.

At 6 is SALEM
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.

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This north coast of Massachusetts has a lot going for it that no one really talks about.

#7 is right here in the Berkshires LENOX, MA
Another small town that’s nestled right here 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.
I Check out interesting attractions like The Mount, Edith Wharton's Home. Lenox is also home to Shakespeare & Company as well as Tanglewood, the summer headquarters of the Boston Symphony Orchestra.

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.

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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.

Rounding out the top 10 NEWBURYPORT
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.


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 great boardwalk.

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