Sun, Sep 21
|Sleepy Hollow
Sleepy Hollow Halloween Fair
Nearly 200 vendors, live music, family fun, and even the Headless Horseman bring festive magic to downtown Sleepy Hollow.
Time & Location
Sep 21, 2025, 10:00 AM – 4:00 PM
Sleepy Hollow, Beekman Ave, Sleepy Hollow, NY 10591, USA
About the event
Experience the enchantment of autumn at the Sleepy Hollow Street Fair, organized by the Sleepy Hollow Tarrytown Chamber of Commerce! On Sunday, September 21, downtown Sleepy Hollow becomes a vibrant festival featuring nearly 200 vendors with unique crafts, tasty food, and local specialties. Wander through the streets to find handmade treasures, savor seasonal flavors, and enjoy live music, family-friendly activities, and the festive atmosphere that defines this community. Don't miss a special appearance by the Headless Horseman himself!