Travel website, The Big 7, is discovering what those of us who live here already know, The Berkshires are pretty dang charming. So charming in fact, that two towns received spots on their 50 Most Charming Towns in The United States list, with one of them taking the top spot. Pretty impressive considering the list highlights iconic destinations like Telluride, Colorado, St. Augustine, Florida and Big Sky, Montana.

Thanks to its extremely diverse population, landscape and culture, the United States is home to an abundance of quirky small towns. We took the time to research the ones that best fit the bill…


....To help us narrow it down, we looked only at communities with a max population of 50,000 that hold a unique quality. Whether your idea of charming small towns equals a mountain village, old rail city, a harbour town or something different entirely, it’s probably on this list.

Coming in at number 29 is Great Barrington.

Great Barrington is known for being one of the country’s most charming small towns. An oasis for nature lovers and art aficionados, there’s something for everyone. Sip on fresh spiced cider from a local farmer, catch a show at Mahaiwe, explore the Catskills or grab a bite and drink at any of the charming small town's gastro gems.

Topping the list at number one was Stockbridge. No surprise that this picture-perfect south county landmark caught the travel site's attention.

Stockbridge looks like something out of a Norman Rockwell painting, and that’s because it is! This cosy New England town was made famous by his portrayal of the city during Christmas. Stockbridge is the ideal New England small-town. Its charming square, constant community events, historic inns, local eateries and preserved homes make it top the list for America’s most charming small towns.


Also receiving a ranking was our neighbor to the north, Bennington, Vermont, coming in at number 28.

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