Stockbridge is in western Massachusetts, about 3 hours from New York City by car and 2.5 hours from Boston. There is no train service directly to Stockbridge; the closest Amtrak station is Pittsfield, about 15 minutes north, on the Lake Shore Limited route from New York. From Pittsfield, a taxi or local bus covers the remaining distance.
By road, take the Massachusetts Turnpike (I-90) to exit 2 (Lee), then Route 102 west to Stockbridge — about 5 minutes. Parking in the village is free and usually available except on peak autumn weekends. A car is useful for reaching Naumkeag, Chesterwood, and the Berkshire Botanical Garden, all of which are slightly outside the walkable village core.