Stockbridge is the quintessence of small-town New England charm, untainted by large-scale development. It is also the blueprint for small-town America as represented on the covers of the Saturday Evening Post by painter Norman Rockwell (the official state artist of Massachusetts). From 1953 until his death in 1978, Rockwell lived in Stockbridge and painted the simple charm of its buildings and residents. James Taylor sang
about the town in his hit "Sweet Baby James," as did balladeer Arlo Guthrie in his famous Thanksgiving anthem "Alice's Restaurant," in which he tells what ensued when he tossed some garbage out the back of his Volkswagen bus down a Stockbridge hillside.
Indeed, Stockbridge is the stuff of legend. Travelers have been checking into the Red Lion Inn on Main Street since the 18th century, and Stockbridge is only slightly altered in appearance since that time. In 18th- and 19th-century buildings surrounding the inn are a handful of engaging shops and eateries. The rest of Stockbridge is best appreciated via a country drive or bike ride over its hilly, narrow lanes.