2 events in Village of Sleepy Hollow, New York

From big races to Saturday morning group runs—find trail running events and connect with the local endurance sports community.

• Rockwood Ramble 10K [friendsrock.org] [Register at runsignup.com]
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  Sat, Jun 06, 2026 at 9:00 AM

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  Starting and finishing in historic Rockwood Hall, our annual Rockwood Ramble 10K is a crowd favorite. Scenic Hudson River views greet runners before the course veers into the woods. The wide carriage...

  Starting and finishing in historic Rockwood Hall, our annual Rockwood Ramble 10K is a crowd 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 Rockefeller State Park Preserve! Race Director Laureen Fitzgerald sees to every detail, ensuring a first-rate experience for all participants. All proceeds benefit carriage road maintenance.

  1k 10k Run Trail

  North Broadway, Village of Sleepy Hollow, New York, 10591, United States
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• Pocantico Hills Races [pocanticohillsmarathon.com] [Register at runsignup.com]
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  Sat, Nov 07, 2026 at 7:00 AM

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  Take on a breathtaking course through the Rockefeller State Preserve, where trails built over a century ago wind past stunning scenery at every turn! Start and finish at Rockwood Hall, with sweeping...

  Take on a breathtaking course through the Rockefeller State Preserve, where trails built over a century ago wind past stunning scenery at every turn! Start and finish at Rockwood Hall, with sweeping views of the Hudson River and the Palisades, just off Route 9 in Sleepy Hollow, next to Phelps Hospital. Both the half-marathon and marathon are single-loop adventures on wide, groomed carriage roads, with the marathon showcasing nearly all of the park’s signature sights. Climb and roll past fields, historic stone walls, charming bridges, grazing livestock, sparkling rivers, lush forests, and peaceful lakes; no pavement, no cars, just pure trail bliss. These races are walk-friendly and offer generous cutoff times, so runners of every pace can join in the fun. Whether you’re chasing a personal best or simply exploring one of the Hudson Valley’s most scenic and historic preserves, the Pocantico Hills Races promise an unforgettable experience!

  13.1 Miles 26.2 Miles Run Trail Walk

  1 Rockwood Road, Village of Sleepy Hollow, New York, 10591, United States
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