The Berkshires has many fine places to dine, high, middle and low ends. I’ve lived in south Berkshire for many years so that is my main area of expertise. There are many good restaurants in Pittsfield, but for old time Italian go to The Highland. The Lantern has won the readers poll for best burgers for years. In Great Barrington, Martin’s Restaurant and The Neighborhood Diner are good stops. A new place in town with an eclectic and vast menu is The Gypsy Joynt – lots of local produce used here, family owned and run. One of the newest dining choices in Great Barrington is the Doughnut Shoppe, right next door to Catherine’s Chocolates – what a choice! I would also recommend Cafe Adam, the chef/owner (Adam) was a student of mine some years ago and is a Culinary Institute graduate. If you stop at the Norman Rockwell Musum in Stockbridge, you can dine on food prepared by the Red Lion Inn.
I’ve left out many places, good luck and have an enjoyable trip.