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The Headless Horseman sends off costumed runners from Beekman Avenue on a 6.2-mile loop through some of the most storied ground in American literature. The certified USATF course winds through the village past the Old Dutch Church, Sleepy Hollow Cemetery, and along the Hudson River with views of the Headless Horseman Bridge. Three water stations …
Enjoy a remarkable course that takes you through Historic Sleepy Hollow’s treasured sights including a stretch along the Hudson River with views of the Headless Horseman Bridge, Sleepy Hollow Cemetery and the Old Dutch Church. You never know what might be lurking on the course in Sleepy Hollow… Registration is limited. Costumes are encouraged but …
Trail and Road Half Marathon Looking for a change of pace? The Sleepy Hollow Half Marathon has the best of fun and scenery. Produced by Rivertown Runners, the 2025 Sleepy Hollow Half-Marathon features approximately 5 miles of carriage roads and groomed trails (crushed gravel and dirt) in the Rockefeller State Park Preserve. The 13.1-mile USATF-certified …
Enjoy a remarkable course that takes you through Historic Sleepy Hollow’s treasured sights including a stretch along the Hudson River with views of the Headless Horseman Bridge, Sleepy Hollow Cemetery and the Old Dutch Church. You never know what might be lurking on the course in Sleepy Hollow… Registration is limited to the first 2000. …
Enjoy a remarkable course that takes you through Historic Sleepy Hollow’s treasured sights including a stretch along the Hudson River with views of the Headless Horseman Bridge, Sleepy Hollow Cemetery and the Old Dutch Church. You never know what might be lurking on the course in Sleepy Hollow… Registration is limited, costumes encouraged but not …
Enjoy a remarkable course that takes you through Historic Sleepy Hollow’s treasured sights including a stretch along the Hudson River with views of the Headless Horseman Bridge, Sleepy Hollow Cemetery and the Old Dutch Church. You never know what might be lurking on the course in Sleepy Hollow… Registration is limited, costumes encouraged but not …
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.