Hillsdale is a rural town in Columbia County, New York, United States. The population was 1,927 at the 2010 census. The town's topography consists of rolling hills (hence its name), open farmland and wooded tracts. It is dotted with many houses, barns and other structures from the 18th and 19th centuries. Hillsdale is a popular area for second-home buyers from New York City, due in part to its proximity to two ski areas and the amenities of nearby Great Barrington, Massachusetts, and Hudson.
The region was taken from the town of Claverack in 1782. The town of Hillsdale was established in 1788.
In 1776 Henry Knox passed through Hillsdale while transporting cannons from Albany, New York, to aid the siege of Boston. There are two markers in Hillsdale along the Henry Knox Trail.
The Dr. Joseph P. Dorr House and Pine View Farm are listed on the National Register of Historic Places.
According to the United States Census Bureau, the town has a total area of 47.9 square miles (124.0 km2), of which 47.7 square miles (123.6 km2) is land and 0.15 square miles (0.4 km2), or 0.34%, is water.