Pittsfield, in the heart of the Berkshires, feels like a small city with a big-heart arts and food scene—walkable downtown cafes, breweries and galleries—plus easy access to hiking, skiing, kayaking and standout cultural sites like Tanglewood, the Norman Rockwell Museum and nearby MASS MoCA, so multiweek stays stay interesting and cozy rather than isolating.
For occasional bigger-city variety, Albany and Springfield are each about an hour’s drive away for expanded dining, shopping and airport options.