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, …

Free

Tarrytown Halloween Parade

Patriots Park Patriots Park, Tarrytown, NY, United States

The 21st annual Village of Tarrytown Halloween Parade steps off at 5:30 pm from Patriot's Park. March south along Broadway to Tarrytown's Main Street. Block party to follow on Main Street: DJ and live music, outdoor dining, performers, and much more! This parade is festive and fun for the whole family. Viewing along the the …

Free

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.