I have talked about Chatham a few times in this blog because of my relationship with it being born and raised. So here are just a few of the things I would recommend doing in Chatham NY.
The Crandell theater is a must for sure. Its a staple in the town and was put on the map for being a historical building. Its a one screen theater with 2 floors of seating,( sometimes the balcony is closed off). They have film festivals and programs through out the year.
Walk around town is something I have done countless times. Going outside of main st and exploring what Chatham has. If your a local you will most likely run into someone you know since its a small town. Many things are in walking distance such as a quick snack at the gas station which you have a few to pick from.
There are many places to have a nice meal in town, if you need a quick bite or a place to sit and eat there are options. There has recently been a few new places that have popped up. My favorite place for sitting down is The Taste Box which is a Mexican restaurant and for a quick bite is Pizza Den. In the summer you cant forget about Donna's. There is also the chatham grill.
There are a few trails and parks outside of the main st such as Ooms pond and the trails behind and around the school/Old Pond. If your just looking for a place to run or bike there is also Bordens pond.
I am into art so my last one is the galleries. There are a few galleries. Thompson Giroux Gallery, Joyce Goldstein Gallery, The Gallery @ Chatham, Park Row Art Gallery but its mostly a frame shop. Galleries usually change there art around every 6 weeks, so you will have something new to see. Theres a new gallery off of main street called Amuse that recently opened up.
There are more things to do in town besides these and agin these are my 5 things I would recommend. If this was made a while ago, I would have said Ralphs Pretty Good Cafe, Clock Tower Toys and a few others. You cant forget about the fair as well. Theres also small events that happen in town but these things can be done all year round. Mac-Haydn Theatre is another thing that happens during the summer, people from all over come.