Trail Running calendar near Woodbury 2025-2026

Rob's Trail Run Edition is a running event taking place at Stillwell Woods Preserve in Woodbury, NY. Scheduled for November 30, 2025, the event features two main races: a 5K Adult Trail Run and a 5K High School or Youth Trail Run, catering to participants of different age groups. This event not only..

The Santa's Summit 10k is a scenic and challenging trail race held along the Bull Run Occoquan Trail at Bull Run Marina. Participants can choose between the 5k and 10k distances, with the event featuring chip timing, finisher medals, and technical event shirts. The course is hilly and partly out-and..

The Tower Tag Challenge is an exciting trail running event held at Sleeping Giant State Park in Connecticut, known for its stunning views and diverse trails. Participants can choose between 4-hour and 8-hour options, racing up and down the Tower Trail, which ascends over 600 feet to the Observation..

The PPTC Endurance Fest is an exciting running event taking place in Prospect Park, Brooklyn, featuring both a 50-mile and a 50-kilometer race. Participants will navigate a looped course that honors NYC's ultramarathon heritage, completing either 9 or 15 loops of 3.33 miles each. The event encourage..

The Frosty Forest 5K is an exciting trail running event taking place in Roosevelt Forest, Stratford, CT. Participants can run, jog, hike, or walk the 5K course while enjoying the beauty of nature and the festive holiday spirit. Costumes are encouraged, adding to the fun atmosphere.Awards will be giv..

The Livingston Oval Ultra is a 2026 ultramarathon event held in Livingston, NJ, featuring races of 1, 3, 6, and 12 hours. Participants run around a USATF-certified, fast, and flat oval course, aiming to cover as much distance as possible within their chosen time frame. The event offers a supportive..

The Squatchapple - West Orange, NJ will take place in West Orange on Saturday 7 March 2026. You can run between 11 and 50 miles.

The Sleeping Giant Trail Runs is a challenging new race set in one of Connecticut's iconic parks, known for its diverse trails. Participants can choose between a 25K and a 50K course, both featuring over 3,000 feet of elevation gain. The event showcases a mix of smooth carriage roads and technical,..