If you're driving over from Albany, take Interstate 90E out of town about 5 miles, and then get on U.S. Rt. 20 East. This takes you through Lebanon, NY, and then over the mountains and brings you right into Pittsfield, Mass, in the heart of the Berkshires. A gorgeous drive in all seasons.
About a mile or so from the intersection of Interstate 90 and U.S. Rt. 20, you hit the intersection of U.S. 20 and U.S. 9. There is a real good cafe at the southeast corner of that intersection. They are well know for their great chili and soups.
Once you are in the Berkshires, don't miss Natural Bridge State Park, in North Adams, and also Hickory Bill's BBQ, also in North Adams. Somewhat pricier but well worth it is the Dakota, which is on the east side of the road between Pittsfield and Lee.