Trail Running Calendar New York 2025-2026

NYC Trail Mix is an annual ultra trail running event held in Staten Island, New York, featuring distances of 50 miles, 50K, and a half marathon. The course showcases over 35 miles of trails through the greenest parts of New York City, including Blood Root Valley, High Rock Park, La Tourette Park, an..

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 PPTC Endurance Fest is an ultramarathon event held in Brooklyn, NY, featuring 50-mile and 50-kilometer race options. The race takes place on a looped course within Prospect Park, consisting of 9 or 15 laps of a 3.33-mile loop. Starting and finishing near the Lincoln Road Entrance, the event hono..

The 0 Degree Winter Trail Festival is a trail running event held in Pittsford, New York, featuring three race distances: 15 miles, 10 miles, and 5 miles. The festival offers a challenging course that includes notable climbs such as the "Hell on roots climb" and the "Ski Hill Climb," providing a rugg..

The Frozen Assets Endurance Run is a winter trail race held at Harriet Hollister Spencer State Recreation Area in Springwater, NY. Scheduled for January 3, 2026, the event features an approximately 10k loop course primarily on winding single-track trails originally blazed for mountain biking. Partic..

Mrs. McCormick's Ice House is a winter trail running event held at Ontario County Park in Naples, New York. Scheduled for January 17, 2026, the race offers participants the choice to complete a 4-mile loop once or twice, totaling up to 8 miles.The course navigates scenic parts of the park, avoiding..

The Devil's Shadow Winter Trail Races take place at Mendon Ponds Park in Honeoye Falls, NY, featuring 5-mile, 25k, and 50k distances. The race course is a roughly 5.1-mile loop around Devil's Bathtub, designed to avoid major hills and road crossings, with the start and finish at Hopkins Point Lodge...

The DENFIT Winter Soldier is a challenging running event held in Cape Vincent, NY, on February 28, 2026. Participants can choose from a full marathon, half marathon, or 10K race, all taking place along a flat, out-and-back course from Cape Vincent Recreation Park to Tibbetts Point Lighthouse. The ev..

Big Bear Squatch North is a challenging trail running event held at Harriman State Park in Bear Mountain, New York. Featuring a half marathon and 10K races, including new rucking divisions with lightweight (15 lbs) and heavyweight (30 lbs) packs, the course offers rugged, technical trails with steep..

The TrailsRoc Last Runner Standing is a unique endurance running event held at Basil Marella Park in Rochester, NY. Participants run repeated 1-mile trail loops in a mass start format, with progressively shorter time limits to complete each loop. Runners who fail to finish within the allotted time a..

Squatchywaska Mountainfest is a challenging trail running event held in Ellenville, New York, featuring two race distances: a 25K and a 10-mile course. Set in the stunning Shawangunk Ridge, runners navigate rugged mountain singletracks, cliffs, and glacially polished ledges through pitch pines, huck..

Leatherman's Loop is a renowned 10k trail race held annually each spring at the Ward Pound Ridge Reservation in Cross River, New York. Established in 1987, it is considered the largest trail race on the East Coast of the United States. The event features a challenging and scenic course through the r..

The Webster Trail Classic is a trail running event held in Webster, NY, featuring a 10-mile race, a 3.5-mile run, and a kids fun run of about 1 mile. The course traverses three neighboring parks—Webster Park, Whiting Road Nature Preserve, and Gosnell Big Woods Preserve—each offering unique trail exp..