STOCKBRIDGE, MASSACHUSETTS

Population: 1,947

Serving as the inspiration for Normal Rockwell’s depictions of Americana on the front page of the Saturday Evening Post, Stockbridge is truly the paradigm of a small New England town. The artist lived in this undeveloped gem in the Berkshires from 1953 until 1978, capturing Stockbridge’s unique character in his paintings. Today, you can visit the Norman Rockwell Museum to see a retrospective of his work; also tourChesterwood, sculptor Daniel Chester French’s summer home. In many ways, Stockbridge feels timeless with its well-preserved architecture from the 18th and 19th centuries, which explains why this has long been a destination for wealthy Bostonians looking for a country escape. What’s more, Rockwell wasn’t the only artist to be inspired by this Massachusetts town; Stockbridge has been immortalized in James Taylor’s “Sweet Baby James,” and in Arlo Guthrie’s classic, droll Thanksgiving monologue-ballad “Alice’s Restaurant.” The town is also home to an eclectic shopping scene and Rouge, a French bistro housed in a shingled cottage just outside of town.

Where to Stay: The Inn at Stockbridge has beautiful grounds, but its proximity to the highway means some rooms are less quiet than others. The Red Lion Inn has been in operation since 1773 and consists of one historic building and nine annexes, each one unique.

Plan Your Trip: Visit Fodor’s Stockbridge

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