The long Main Street runs between old maples and white porches, with the Red Lion Inn, a sprawling clapboard hotel with a rocking-chair porch, anchoring the middle. Norman Rockwell lived and worked here from the 1950s until he died in 1978, and his painting of this very street, wrapped in snow and Christmas lights, is among his best-loved pictures. The museum that carries his name sits on a hillside just outside the village.
Stockbridge's story starts before the colonists. The place was a mission town for the Mohican people, and the Stockbridge-Munsee community, whose ancestors were here, still exist, now based in Wisconsin. Later it became a gathering place for writers, artists and sculptors. Daniel Chester French, who made the seated Lincoln in Washington, had his summer studio at Chesterwood, a short ride away, and the grounds and workshop are open to visitors in season.
For riding, the surroundings are gentle but absorbing. Route 7 runs along the valley floor, and Route 102 and the lanes between Stockbridge, Lee and West Stockbridge go through hardwood forest, past old farms and over the quiet Housatonic River. The corners are easy, the traffic can be heavy in summer and on foliage weekends, and the surface suffers from the usual New England frost damage. Early morning is the time to enjoy the village without tour buses, and September and October bring the colours that people travel across the world to see. Winter is cold and the roads can ice, so most bikes are in the shed.
The Berkshires are known for culture, so you will find a lot going on, including the Berkshire Theatre and music at Tanglewood, a few kilometres north. There are good places to eat on and around Main Street, with a mixture of tavern fare and more modern cooking, and parking along the street is easy outside the busy weekends.
Fuel needs a little planning. Stockbridge is a village of just over two thousand people, and its stations are limited, so Lee, six kilometres away, or Pittsfield, nineteen, are the sensible places to top up before heading into the hills.