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

Plein Air Painting

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

Experience nature through painting! Learn the watercolor technique under the guidance of award-winning artist, Anne Johann, as you absorb the beauty of the landscape at Rockefeller State Park Preserve. You may bring your own supplies if you have them; if not, supplies will be provided. Recommended supplies include: a watercolor set, paintbrushes, watercolor paper, pencil, …

$8

Plein Air Painting

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

Experience nature through painting! Learn the watercolor technique under the guidance of award-winning artist, Anne Johann, as you absorb the beauty of the landscape at Rockefeller State Park Preserve. You may bring your own supplies if you have them; if not, supplies will be provided. Recommended supplies include: a watercolor set, paintbrushes, watercolor paper, pencil, …

$8

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

Come run the Pocantico Hills Marathon or Half Marathon in Rockwood Hall portion of Rockefeller State Park Preserve! These single loop courses are rolling and hilly with views of the Hudson River and Palisades. Run past fields, stone walls and bridges, lakes and streams, forests and grazing livestock! The course CLIMBS A LOT, rocking and …

$60 – $150

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.