The Point at Thornwood Inn, Great Barrington
I may get skewered by foodies for this one, but we had dinner at this place on Saturday night -- after passing by for many years -- and enjoyed it very much. The food (Caesar salad and roast pork loin) was fine, although it won't knock your socks off, reasonable, kind of old-fashioned, and delightful piano music on Fridays and Saturdays. The dining room was comfortable, with a lovely view of the garden from our window seats, and the service was just right. I would choose this over what I consider many overpriced "fine" food establishments in Lenox, Great Barrington, etc. Would definitely return.