Trail Running Calendar New York 2025-2026

Rob's Trail Run Edition is a trail running event held in Woodbury, New York, at Stillwell Woods Preserve. Scheduled for November 30, 2025, the event features two main races: a 5K Adult Trail Run for participants aged 19 and older, and a 5K High School or Youth Trail Run for those 18 and under. The c..

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. This event honors New York City's road ultra heritage, following in t..

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 serves as a fundraiser to support various trail projects in the area. The course includes challenging features such as the "Hell on R..

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 of completing a 4-mile loop once or twice, navigating scenic trails that avoid deep snow drifts.As part of the Common Gr..

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 winter running event held in Cape Vincent, NY, featuring a flat, fast out-and-back course along the icy St. Lawrence River from Cape Vincent Recreation Park to Tibbetts Point Lighthouse. Participants can choose from a 10k, half marathon (two laps), or full..

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 a unique rucking division with lightweight (15 lbs) and heavyweight (30 lbs) categories, the course offers rugged, technical trails w..

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..

The John Jay Community Trail Race, held in Cross River, NY, is a competitive 5k run on the newly developed John Jay Community Cross Country Trail. The course begins on the lower fields of the John Jay Campus, quickly entering challenging, hilly wooded trails near the middle and high schools, and fin..

English's Ridge Rumble is an annual trail running event held at Green Lakes State Park in Fayetteville, NY. The race offers three distances: 50km, 20 miles, and 10 miles, with a challenging 10-mile loop featuring about 1,300 feet of elevation gain. The course showcases scenic and technical trails, i..

The Squatchywaska Mountainfest is a challenging trail running event held in Ellenville, New York, featuring two distances: a 25K (approximately 17 miles) and a 10-mile race. Set in the scenic Shawangunk Ridge, runners traverse rugged mountain singletracks, including pitch pines, huckleberry bushes,..

Leatherman's Loop is a popular 10K trail race held annually in the spring at Ward Pound Ridge Reservation in Cross River, New York. The event attracts runners aged 7 to 107 and features a scenic course through natural trails. Due to high demand, entry is determined by a lottery system.The registrati..

The VCP50k is an ultramarathon held in Bronx, New York, founded in 2023 and designed to accommodate both novice and experienced runners. The race features a challenging yet accessible course consisting of ten loops on the classic Tortoise and Hare cross country trail, plus an initial lap on flat ter..

The Medved Madness Trail Races, held annually at Mendon Ponds Park in Honeoye Falls, NY, is a popular spring trail running event featuring two main races: a Long Course of approximately 13 miles and a Short Course of about 5 miles. The course varies each year due to trail conditions, with a basic ai..

Breakneck Point Trail Runs, hosted by Red Newt Racing, take place at University Settlement Camp in Beacon, New York. The event offers two challenging distances: a half marathon of 14.5 miles with approximately 4,800 feet of elevation gain, and a full marathon of 26.4 miles with about 9,000 feet of g..

Run The Farm is a scenic trail race series held at Muscoot Farm in Katonah/Somers, New York. The event features a 5-mile trail race along with two kids' races tailored for different age groups, promoting family participation. The race showcases the natural beauty of Muscoot Farm, a working farm and..

Cayuga Trails is a scenic ultramarathon event held at Robert Treman State Park near Ithaca, NY, featuring two challenging distances: a 50-mile race with approximately 10,203 feet of elevation gain and a 50K covering 31.6 miles with about 6,882 feet of gain. The course is predominantly singletrack tr..

The Plattekill Mountain Race, held in Roxbury, NY, is a challenging trail running event featuring a 6.5-mile course with 3,500 feet of elevation gain. The race traverses the ski slopes and trails of Plattekill Mountain, offering a rigorous mountain challenge suitable for those seeking a tough traini..

The Table Rock Trail Challenge is an annual Last One Standing trail running event held at Clark Reservation State Park in Jamesville, NY. Celebrating its 10th year, the race features looped courses of approximately 1.2 to 1.3 miles, traversing diverse terrain including crushed gravel, slick limeston..