Working in radio, I’ve gotten a chance to move across the country. One of the places I lived for five years was Louisville, KY. One of their claims to fame besides the Hot Brown and The Kentucky Derby was Bardstown, KY. Rand McNally and USA Today called it the “most beautiful small town in America.”

According to a new article in, that’s not the case anymore. Stockbridge in the Berkshires topped the list of the 50 most charming small towns in America.

Big 7 Travel says that “Stockbridge looks like something out of a Normal Rockwell painting, and that’s because it is!” What are they talking about? Well Rockwell made it famous in one of his Christmas paintings. So what else makes Stockbridge the best of the best? Big 7 Travel continues “the charming town square, historic inns…local eateries…all make it the ideal New England town.”

Massachusetts wasn’t the only New England state to make the list though. Vermont was also represented in the top 50 with a nod to Woodstock at No. 2. New Hampshire was also in the top 10 with the #4 spot going to Sugar Hill, NH and #7 slot going to Meredith.

What’s your favorite small town in New England?

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