A place called "Northern Galapagos" on OLD route eight in Torrington, one of my favorite restaurants in CT. It's a Chilean joint. Right next door is Nejaim's, a Lebanese deli that is also top notch. I've been to West Street Grill, I liked it quite a lot. Bantam Bread on route 202 east of Litchfield has good EXPENSIVE stuff. I've been to Carol Peck's a couple of times.... meh. I'd rather go to "The Charcoal Chef" on route six north of Woodbury! It's a "Blue Hair" hangout. Kind of 1950ish place, the cocktails are made right, and strong!
The Black Rock Cafe in Thomaston is getting rave reviews from all my foodie friends.
Peaches and Cream on Route 202 is the best ice cream place in the State, although the "Canton Creamery" on rte 44 is pretty damn close.

Awesome pancakes and homemade split grilled sausage at the "Roadside" in Monterey on Route 23. They make their own bread there, too. Real maple syrup, don't order the extra unless you are a serious sugar fiend, they give you quite a lot.
The place is certainly "roadside" in character. It's part of a foundation that runs a farm up the road.
The Thai place in Great Barrington is pretty good, too. The Williamstown Inn has good food, pricey, though.
Best food I've ever eaten in Massachusetts was a place called "La Tomat" in Great Barrington; heard it's closed now, though.