Another of my favorite Berkshire destinations are the Norman Rockwell Museum grounds. Every year they have a delightful, themed sculpture exhibition. It is free to the public. You can wander around, bring a picnic lunch and enjoy the spectacular views from the top of the hill. Rockwell's studio is also there but they moved it to the hilltop from it's original location in Stockbridge. He never actually painted there but it is still interesting and a beautiful location.