Sleepy Hollow Street Fair

Beekman Avenue, Sleepy Hollow Beekman Avenue, Sleepy Hollow, NY

The Sleepy Hollow Tarrytown Chamber of Commerce’s annual Sleepy Hollow Street Fair takes place this year on Saturday, October 8th, transforming Beekman Avenue into an outdoor market. October is the most exciting time to visit Sleepy Hollow. The weeks leading up to Halloween have something for everyone: haunted hayrides, Gothic mansions, blazing pumpkins, farmers markets, live music, 5K …

Free

There’s something for everyone in the real Sleepy Hollow—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 5K run, Halloween parade, and of course, the Headless Horseman! For the latest on Fall events, visit our guide to Halloween in Sleepy Hollow.