Stockbridge is a tiny Berkshires village near the New York State line — basically a single block of Main Street at a T-junction — but it punches well above its weight.
The Red Lion Inn, built in 1773, still operates as a country inn and is worth a stop for a meal even if you are not staying. It is one of the oldest continuously operating inns in the United States.
Stockbridge's biggest claim to fame is Norman Rockwell, who lived and painted here for the last twenty-five years of his life. His studio was originally on Main Street — the very street he depicted in his iconic Saturday Evening Post covers of small-town America. The Norman Rockwell Museum has since moved to a larger property just outside town, where you can see the original studio and the most comprehensive collection of his work anywhere.
Beyond Rockwell, Stockbridge holds more than its size suggests. Naumkeag is a 19th-century hilltop estate with some of the most inventive garden design in New England. Chesterwood was the working studio of Daniel Chester French, sculptor of the Lincoln Memorial — the studio railroad track he used to check his models in natural light is still there. The Mission House is the oldest building in town and honestly confronts the colonial history behind the village's picturesque surface. South of the village, Ice Glen is a glacial ravine where ice persists into summer — one of the more genuinely dramatic natural features in the Berkshires and almost always empty of other visitors.
The surrounding Berkshires countryside is beautiful in any season, but autumn is spectacular. Stockbridge also sits close to Tanglewood, the summer home of the Boston Symphony Orchestra, and the town makes a good base for exploring the rest of the Berkshires.