Pittsfield is the practical capital of the Berkshires, less polished than Stockbridge and less precious than some of the smaller hill towns. That is part of its appeal. It has working-city bones, good cultural institutions, and quick access to the wooded ridges and lakes that make western Massachusetts so inviting.
The city is best known to literary travelers for Arrowhead, the farmhouse where Herman Melville wrote Moby-Dick. Downtown, Park Square, the Berkshire Museum, the Colonial Theatre, and Barrington Stage Company give Pittsfield more cultural weight than its size suggests.
It is also a good base if you want the Berkshires without committing to a postcard village. Hancock Shaker Village sits just west of town, Onota Lake and Pontoosuc Lake cover the easy-outdoors side, and the surrounding hills turn riotously colourful in autumn.