Sunset Hike at Rockwood Hall

Rockwood Hall 1 Rockwood Road, Sleepy Hollow, NY

Join this 3-mile sunset hike at Rockwood Hall for what the organizer hopes will be a spectacular view over the Hudson River and the Tappan Zee Bridge. Please dress according to weather conditions and bring water. Leashed dogs are welcome. This hike is at Rockwood Hall, DO NOT go to the main Preserve entrance. The parking …

$3

Rockwood Ramble 10k

Rockwood Hall 1 Rockwood Road, Sleepy Hollow, NY

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! …

$20 – $50
Recurring

History of Rockwood Hall

Rockwood Hall 1 Rockwood Road, Sleepy Hollow, NY

Join park Historian, David Teich, on an adventure into the past as he explores Rockwood Hall and its rich history through stories of the land and the people who called it home. Former estate of William Rockefeller, this site boasts scenic views overlooking the Hudson, lush forests, and remnants of 19th century luxuries. Leashed dogs …

$3
Recurring

Wildflower Walk

Rockefeller State Park Preserve 125 Phelps Way, Pleasantville, NY

Join wildflower expert Patty Butter for a leisurely walk and learn about the identification of spring ephemeral wildflowers. Contribute as a citizen scientist to increase our knowledge of the ecology of the Preserve by logging your observations in the iNaturalist app. Bring a camera or cell phone to take pictures and add the iNaturalist app …

$3

Rocky’s 5k

Rockefeller State Park Preserve 125 Phelps Way, Pleasantville, NY

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 …

Pocantico Hills Marathon

Rockwood Hall 1 Rockwood Road, Sleepy Hollow, NY

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 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.