Nicest town to visit & stay in, in the Berkshires MASSACHUSETTS?

The major towns are Pittsfield, Lenox, Stockbridge and Great Barrington. There are a lot of small towns with nice resort hotels and B&B's, but those four are the only towns with significant shopping and other activities.

I would rank Great Barrington as the nicest of the lot, with Lenox, Stockbridge and Pittsfield falling in behind them. Lenox has a lot of nice restaurants (more than Great Barrington), but the shopping is mediocre. Stockbridge is essentially a one-horse town - you have the Red Lion as the hotel with its collection of restaurants, and that's about it. Pittsfield is the largest town, but unlike the others it's an old factory town that's a bit worn about the edges.

While in the area, be sure to visit Williamstown and North Adams. Williamstown has a great little college and a world-class art gallery (the Clark Institute), and North Adams has MassMOCA which is a fabulous place to visit.

Stockbridge is really nice. If you're looking for a hotel, try the Red Lion Inn. It's a really old hotel, but it's gorgeous. Also, Lenox is a great place as well. Same with Great Barrington.

Stockbridge and Lennox area.