3. Callicoon
Callicoon, located on the New York-Pennsylvania border, has more hipster influence than the previously mentioned towns. Its Main Street is lined with antique and consignment shops, albeit pricier ones than can be found in Roscoe or Livingston Manor. There is a farmer’s market located behind Main Street at Callicoon Creek that one can visit every Sunday from 11 a.m. until 2 p.m. Here visitors can try local wines, jams, and cheeses while taking in some Catskill charm.
Located on the Delaware River, Callicoon also has many water sports to offer including kayaking, canoeing, tubing, and anything else one could find themselves wanting to do on a large river. Its downtown area is decked out with shops and historic buildings all still proudly showing off their vintage exteriors. The most impressive one may perhaps be the Western Hotel located on Main Street. An old Victorian mansion, it was originally opened as an inn in 1852 and has ten guest rooms that are still used today by guests from all over who come to find a quaint yet charming getaway destination.