3 running, swimming, and triathlon events in Village of Sleepy Hollow, New York
From big races to Saturday morning group runs—find running, swimming, and triathlon events and connect with the local endurance sports community.
Village of Sleepy Hollow
3 events in Village of Sleepy Hollow-
Sat, Jun 06, 2026 at 9:00 AMSee full details
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.
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Sun, Aug 30, 2026 at 8:00 AMSee full details
This is a beautiful and challenging two and half mile swim across the majestic Hudson River from Nyack, NY to the historic village of Sleepy Hollow, NY.
Our goal is to give swimmers the opportunity to enjoy the panoramic views as they swim across the scenic Hudson River while supporting Feeding Westchester and other local charities.
All swimmers must have proof of open water experience or must have a life guard or swim coach sign off on their ability. This proof can be uploaded at time of registration or sent to the [email protected] by August 26th at the latest. Proof can consist of results from a prior swim event or triathlon. If this is not available a swim coach or lifeguard can sign off on the swimmer's capability to swim across the Hudson River. All swimmers will be required to wear a safety buoy which will be supplied at the event. The swim must completed in three hours.
The Lighthouse Swim is a charity event, and we carefully plan and budget based on participant registrations and commitments made in advance. For this reason, all registration fees and donations are non-refundable. We highly recommend signing up for race insurance.
If you are unable to participate, you may request a deferral prior to the event, subject to approval and applicable deadlines.
In the event the swim is canceled due to weather, safety concerns, or circumstances beyond our control, registration fees and donations will not be refunded. The Lighthouse Swim takes place rain or shine; however, the safety of our swimmers, volunteers, and community is our top priority.
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Sat, Nov 07, 2026 at 7:00 AMSee full details
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!