Trail Running calendar near Garrison 2025-2026

The Tesla Hertz Run is an exciting running event taking place in Rocky Point, NY, featuring various race distances including a 150 Miler, 100 Miler, 100K, 50 Miler, 50K, and 10 Miler. Set in a picturesque area of Long Island, the course offers a scenic 10.48-mile loop through the pine barrens, provi..

The Forbidden Forest 30 Hour Ultra Run is an exciting endurance event set in Stratford, CT, where participants can run, power-hike, or walk for up to 30 hours. This ultra run offers various distance options, including 26.2M, 50K, 50M, 100K, and 100 miles, allowing runners to challenge themselves at..

The Mohawk Mountain Race, organized by Steep Endurance, takes place at the Mohawk Mountain Ski Area in Cornwall, CT. This unique event transforms the ski mountain into a challenging running course featuring 5K, 10K, Half Marathon, and Marathon options. Participants will navigate steep ascents and de..

The Paine to Pain Trail Half Marathon is a scenic race set in Westchester County, New York, featuring a unique course that traverses the woods and trails of five different parks. This challenging half marathon offers participants a chance to experience nature while running predominantly on dirt trai..

Big Bear Squatchtoberfest is a trail running event hosted by Sassquad Trail Running and the New York-New Jersey Trail Conference, taking place at Harriman State Park in Tuxedo, New York. Participants can choose between a challenging half marathon and a 10K, both featuring rugged terrain, steep climb..

Run The Farm is a trail running event scheduled for October 19, 2025, at Muscoot Farm in Katonah, NY. The event features a 5-mile race for adults and two kids' races: one for ages 7-12 and another for children aged 6 and under. Participants can enjoy the scenic beauty of the farm while promoting awa..

The Bimblers Bluff 50K is an off-road foot race held in southern Connecticut, starting at Guilford Lakes School. The course features rolling forest roads and rocky single tracks, providing a challenging experience for runners. Unlike many similar events, participants do not complete the same loop mu..

The Fall Back Into The Trails Series is an annual running event hosted by C.T.W Endurance, taking place at the Red Wing Recreation Area in Lagrangeville, NY. Scheduled for November 1-2, 2025, the series features three race options: a challenging 100k, a 50k, and a 10k, each with varying elevation ga..

The Long Run - Fall Back is a unique running event taking place at Jacobsburg State Park, featuring a 5-mile loop that combines single track and gravel trails. Participants can choose to compete in a 5-mile race, a 3-hour, or a 6-hour event, with the course run in reverse for this rendition. The eve..

The "8 Hours at the Farm" is a trail running event organized by Steep Endurance, taking place at Gurski Farm/Williams Park in Brookfield, CT. This event features a scenic, approximately 4-mile loop course that includes single track and rolling farm trails, fostering a vibrant community atmosphere am..

The Pocantico Hills Marathon, taking place in Rockefeller State Park, offers both a marathon and a half marathon on scenic, rolling courses with views of the Hudson River and Palisades. Participants will enjoy a picturesque route featuring fields, stone walls, lakes, and forests. The event supports..

The Raven Rocks 10k is an annual trail race held at the Ward Pound Ridge Reservation in Cross River, NY. Set against a scenic backdrop, the race features a challenging course that includes rocky climbs, ridgeline trails, and hilly meadows. The event not only promotes fitness and outdoor activity but..

NYC Trail Mix is an exciting ultra trail running event taking place in Staten Island, New York, on November 15, 2025. This event features three race distances: a 50-mile, a 50K, and a half marathon, all set against the backdrop of over 35 miles of scenic trails. Participants will explore unique loca..

The Tarrywile Half Marathon is a challenging trail race set in Tarrywile Park, Danbury, Connecticut. Known for its tough terrain, the course features significant elevation gain of nearly 3,000 feet and technical Northeast single track paths. Participants can choose from three distances: a Half Marat..

The Fall Fling 400 is an annual trail running event organized by the CT Trailmixers, featuring a unique 400-minute race where participants can complete as many loops as they wish on a two-mile course. Additionally, a 4-mile option is available, consisting of two laps of the same course. The event pr..

The Squatchy Leftovers Trail Race, taking place on November 29, 2025, at South Mountain Reservation in West Orange, NJ, offers a variety of distances including 5K, 10K, 25K, and 50K. This family-friendly event supports the non-profit organization Bigger Than The Trail, which provides cost-free thera..

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 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..