Hillsdale is a town in Columbia County, New York, near Hudson, New York and Great Barrington, Massachusetts. State routes 22 and 23 intersect near the town center, which is listed on the National Register of Historic Places. The town has several restaurants and a general store, among other businesses. Hillsdale is known for its hilly landscape and is near Bash Bish Falls, Taconic State Park, and the Catamount Ski Area. The Harlem Valley Rail Trail, a 26-mile bike path in two sections, is located not far from the intersection of routes 22 and 23.

Columbia County is a county in the U.S. state of New York. At the 2020 census, the population was 61,570. The county seat is Hudson. The name comes from the Latin feminine form of the surname of Christopher Columbus, which was at the time of the formation of the county a popular proposal for the name of the United States. The county is part of the Capital District region of the state.