Good food in the Berkshires
There are a lot of good threads on this subject. I agree with John Andrews, Bizen and Inn on the Green. They are probably the three best, with Bizen being right on Railroad Street in town. The others are a short drive away but well worth the trip for a special night. The Old Mill in South Egremont is surprisingly good, as well. If you like BBQ, try the Route 7 Grill, just south of downtown.
As far as downtown,you can't beat the pizza at Baba Louie's. It's really good, even if you do not usually go for pizza. Castle Street has a nice bar with a good wine selection and often has music. Martin's is very popular for breakfast. Do a search on this board for a lot of very detailed information and reviews. Have fun.