Hillsdale is known for its hilly landscape and is near Bash Bish Falls, Taconic State Park, and the Catamount Ski Area.

[2] Around 1745, Martin Krum is reported to have purchased 800 acres in the western portion of the town from the Van Rensselaer family.

Robert Noble and his associates procured the Indian title to land about five miles square in the eastern part and called it Nobletown.

The Van Resselaers and the Livingstons leased land on their vast estates to tenant farmers, but those who had emigrated from Massachusetts did not recognized the landlords' titles.

In 1776 Henry Knox passed through Hillsdale while transporting cannons from Albany, New York, to aid the Continentals in the siege of Boston.

Falcon Ridge Folk Festival takes place every August on Dodds Farm, 4.5 miles (7.2 km) north of the intersection of routes 22 and 23.

Additionally, the Oldtone Music Festival is held at Cool Whisper Farm on Route 21 in early September.

Grass Fed Arts/Oldtone preserves roots music and traditional folkways through artist and audience participation; connecting neighbors, bridging cultures, and sharing insight and wisdom across generations.