Rocky’s 5k

Rockefeller State Park Preserve 125 Phelps Way, Pleasantville, NY, United States

Run like a headless horseman is after you! Beautiful fall foliage is the perfect backdrop for Rocky’s 5K. Challenging hills and wide carriage roads – the perfect race for experienced trails runners and first timers. If you are familiar with the Rockies, test your stamina and charge those uphills! First 5K? The well-marked course and …

$25 – $45

Pocantico Hills Marathon & Half Marathon

Rockwood Hall 1 Rockwood Road, Sleepy Hollow, NY, United States

This challenging and beautiful course begins and ends at the Rockwood Hall portion of Rockefeller State Park Preserve overlooking the Hudson River and the Palisades. This is just off Route 9 in Sleepy Hollow, next to Phelps Hospital. Both the half marathon and marathon are single loop courses almost entirely on wide groomed carriage roads, and …

$75 – $200

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.