Sleepy Hollow Music Festival

Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United States

The Headless Horseman rides again, but this time he’s heading for the main stage at Sleepy Hollow’s Kingsland Point Park, with its breathtaking view of the Hudson River, for the inaugural Sleepy Hollow Music Festival on Saturday, June 8, 2024. Organizers have announced an inspiring line-up of internationally-touring bands and music festival standouts featuring headliners …


Sleepy Hollow Sprint Triathlon

Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United States

A half-mile swim in the Hudson River, 11-mile scenic bike ride through the legendary village, 3-mile run along Hudson River Walk. All proceeds of the Sleepy Hollow Sprint Triathlon will benefit the Village of Sleepy Hollow Recreation Department’s Teen Summer Camp. The underlying goal of the summer day camp is to provide the children of the community …

$145 – $200

Sleepy Hollow Street Fair

Beekman Avenue, Sleepy Hollow Beekman Avenue, Sleepy Hollow, NY, United States

The Sleepy Hollow Tarrytown Chamber of Commerce’s annual Sleepy Hollow Street Fair takes place this year on Saturday, October 14th, transforming Beekman Avenue into a huge outdoor market. Nearly 100 vendors draw thousands of visitors! October is the most exciting time to visit Sleepy Hollow. The weeks leading up to Halloween have something for everyone: haunted hayrides, …


There’s something for everyone in Sleepy Hollow Country—farmers markets, live music, street fairs, historic homes, hiking trails, kayaking and boating on the Hudson River. Halloween season brings even more for the whole family—haunted hayrides, blazing pumpkins, costumed 10K run, Halloween parade, and of course, the Headless Horseman! For the latest on Fall events, visit our guide to Halloween in Sleepy Hollow.