Event Series Local Lore and Legends

Local Lore and Legends

Park Manager Residence 25 Sleepy Hollow Road, Sleepy Hollow, NY, United States

While Sleepy Hollow is well known for its headless horseman, there are quite a few lesser-known legends that take place on this land. The names of some of our most iconic locations such as Spook Rock, Ravens Rock, Witch’s Spring come from stories that have been told by locals dating back hundreds of years. Join …


Rockwood Ramble 10k

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

Starting and finishing in historic Rockwood Hall, the annual Rockwood Ramble 10K is a favorite. Scenic Hudson River views greet runners before the course veers into the woods. The wide carriage roads provide the perfect setting for experienced trail runners and first timers. Say goodbye to traffic, pavement and noise and hello to the Preserve! …

$30 – $50

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

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.