I came to Stockbridge, in The Berkshires, for the first time this August. It's a 2hr drive west of Boston. The drive to get to Stockbridge is beautiful, beautiful, beautiful. I took Mass Pike all the way almost to the very end (to exit 2!). I would love to go again during the fall when the leaves change color. It's just breathtaking.
My trip to Stockbridge was also my first trip to Tanglewood in Lenox, MA.
"Unique New England Town"
Stockbridge is a great town to visit no matter the season. Many people associate the town with Norman Rockwell as many of his paintings feature the local residents.
Most people like to stay the the Red Lion Inn. Located on Rt. 7 in the center of town, an Inn or stage coach stop has been in this spot since pre-revolutionary days.
The Red Lion Inn has a very nice resturant so if you can't afford to stay here(it's rather expensive), you can still come and enjoy a lovely meal or afternoon tea. People watching from a rocking chair on the large front porch is a relaxing pass time as is checking out the eclectic shops along Main Street.
From here, day trips to the surrounding area are quick and easy. You can even venture into Connecticut, Vermont, or New York.
During the summer months you can attend a concert at Tanglewood, summer home of the Boston Synphony in nearby Lenox. Golf, tennis, skiing, and hiking can also be found locally.