The most charming small town in America is in Massachusetts, according to Big 7 Travel

Ten small towns in New England made the list of 50.

Main Street in Stockbridge at Christmastime. Stockbridge Chamber of Commerce

A town in Massachusetts made famous by Norman Rockwell is the most charming small town in America, according to Big 7 Travel.

Stockbridge in the Berkshires ranked No. 1 on the travel website’s list of 50 most charming small towns in America, released earlier this month. Big 7 Travel called it “the ideal New England small town” due to its charming square, historic inns, preserved homes, community events, and local eateries.

“Stockbridge looks like something out of a Norman Rockwell painting, and that’s because it is!” Big 7 Travel wrote. “This cosy New England town was made famous by his portrayal of the city during Christmas.”


Woodstock, Vermont, snagged the No. 2 spot on the list because “you can enjoy delicious farm-to-table meals, endless scenic trails, and then experience its rural heritage without ever getting on a highway,” Big 7 Travel wrote.

A total of 10 New England small towns made the list. The towns had to have a maximum population of 50,000 and “hold a unique quality,” according to Big 7 Travel.

Here are the New England towns that made the cut and how they ranked:

1. Stockbridge, Mass.
2. Woodstock, Vermont
4. Sugar Hill, N.H.
7. Meredith, N.H.
11. Mystic, Conn.
13. Stowe, Vermont
26. Nantucket, Mass.
28. Bennington, Vermont
29. Great Barrington, Mass.
49. Montpelier, Vermont
View the entire list of the 50 most charming small towns in America.


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