Old Chatham is the sort of place you can visit without noticing. Aside from the Old Chatham Country Store, there isn't much of a downtown to speak of, just a few blocks lined with aging mansions. Just on the New York side of the Massachusetts border, the town is notable mostly for being beautiful and seeming far more remote than it is. A short drive puts you in New England college country or Kinderhook, a town thick with Manhattanites and restaurants run by recent graduates of the Hyde Park's Culinary Institute of America. Bring a bike and you'll never be bored.
What to Do for Fun: If you're determined to have a good time within the borders of the town, you'll want to start pedaling or head for Old Chatham Sheepherding Company, where you can buy some of the best cheese on the East Coast and hang out with some ungulates in a no stress environment. The place is also a bit of a destination for birders. Again, you'll want to have a bike to chase woodpeckers down country roads.