A great place, and not a terribly long ride from some other great, light hikes and great barrington Mass. You would also be near some great places in litchfield county CT, including my beautiful hometown (winsted/winchester) which boasts a beautiful lake, great hiking, cool historical stuff (most of it reportedly hauted) and great restaurants (surprisingly great). There are some bed and breakfasts, and hotels in nearby torrington, and all over the berkshire area. If you don't want to drive, you can take a bonanza bus from penn station to Torrington, Winsted, or a number of towns all the way up to Pittsfield, Mass, and I know plenty of places where you can stay, and people and companies who would give you a lift anywhere you would need to go. You could also take the Metro North all the way up to Waterbury...
Or, you could do the Labor Day weekend thing and take the Metro and the Shoreline east to Mystic, Old Saybrook, or get over the Rhode Island border and hang out on the beach and booze in Westerly/Misquamicut (sp?).