Hey, I live in Housatonic! She is moving to Monterey, perhaps?
The Roadside Grill in Monterey is great for breakfast! The best pancakes. The Edith Wharton house is lovely. The Red Lion Inn is nice, as Cyn said. I have heard that Prime in Lenox is good (steak house), but pricy--I have not eaten there. There is also Cafe Zinc in Lenox. Betty's Pizza Shack has great pizza and a surf shack theme. More casual, of course! Be prepared to pay "summer in the Berkshires" prices at most places. Viva in Glendale (between Housatonic and the Norman Rockwell Museum) is also good. Spanish place w/tapas and paella. If you want more upscale, try Old Inn on the Green in New Marlboro. Very nice, pricey, but they are doing a prix fixe menu on Sundays, if you are going to be around then. You can get fabulous sushi (and tempura, noodles, etc) in Great Barrington at Bizen. Also heard that Allium in Gt. Barrington is good. Also a good mexican restaurant in GB, but can't spell it for the life of me: xichotachal...something with these letters! Hope I helped some. Places seem to come and go these days, as does quality--given the economy. Let me know how your visit turns out.