Trail Running Calendar New York 2025-2026

Squatchywaska Mountainfest is a mountain trail race in Ellenville, NY, offering two courses: 25K and 10 miles. Runners traverse rugged singletrack, cliffs, and crushed-gravel carriage roads on the Shawangunk Ridge, with about 2,500+ ft of elevation on the 25K and around 1,800 ft on the 10M. The rout..

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..

DENFIT ULTRA is held in Cape Vincent, New York (ZIP 13618). The event offers two ultra distances: DENFIT ULTRA 50k and DENFIT ULTRA 100k, inviting endurance runners to push their limits. The page emphasizes a raw, no-nonsense atmosphere with lines like “TEST YOURSELF” and “This isn't your ordinary U..

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..

Breakneck Point Trail Runs in Beacon, New York, is hosted by Red Newt Racing and offers two distances: 21K and 42K, with steep elevation gains (about 4,800 ft and 9,000 ft, respectively). The course blends jeep trails, single-track, historic estate paths, and technical pitches, including the signatu..

Medved Madness Trail Races are held at Mendon Ponds Park’s Stewart Lodge in Honeoye Falls, New York. The event features two trail distances: a Long Course around 13 miles and a Short Course around 5 miles, with the course varying each year based on trail conditions. An Early Start option is availabl..

Sand to Serengeti is a trail-running event held at Green Lakes State Park in Fayetteville, New York. It offers two distances: a 10-mile trail run and a 3-mile option. The route starts on the sandy beach at Green Lakes, winds around Round Lake, climbs toward what locals call the Serengeti, then circl..

Run The Farm is a series of trail races held at Muscoot Farm in Katonah/Somers, NY (51 Route 100, Katonah, NY 10536). The event includes a 5 mile trail race and two age-group kids races (one for ages 7-12 and one for ages 2-6). The spring race is scheduled for May 17, 2026 and the fall race for Oct..

The Mills Miles is a Last Runner Standing format race held at Powder Mills Park in Pittsford, NY, with Race HQ at Powder Horn Lodge. The event uses a one-mile trail loop. Each loop is a mass start with a predetermined cutoff; 25 laps have time cutoffs and a 26th lap is an all-out final race. The co..

Cayuga Trails is a scenic ultramarathon held annually at Robert Treman State Park near Ithaca, NY. The event features two challenging distances: a 50-mile race with approximately 10,000 feet of elevation gain and a 50K covering about 7,000 feet. The course is predominantly singletrack trail (95%) wi..

Lucifer’s Crossing is a trail running event held at Old Y Camp in Robert Treman State Park, Ithaca, NY. It offers three distances: a half marathon (13.2 miles), a 10K (~6.66 miles), and a 5K (3.3 miles). The course features scenic and flowing trails, beginning with a rolling ascent on the wooded Rim..

Plattekill Mountain Race returns to Roxbury, NY for the fourth edition, offering a challenging mountain course on the slopes and trails of Plattekill. The Mountain Race covers 6.5 miles with 3,500 feet of elevation gain, looping up, down, and around the ski area for views and a tough test of enduran..

YMCA Race Weekend is a long-running, volunteer-powered multi-sport festival at Green Lakes State Park in Fayetteville, New York. The two-day event features Saturday options including a Sprint Triathlon (800-yard swim, 12-mile bike, 3-mile run), Aquabike, Aqua Run, and Relay, plus Sunday’s 8K Trail R..

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..

Manitou’s Revenge is a challenging 53-mile ultramarathon held in the Catskill Mountains, starting in Windham, NY, and finishing in downtown Phoenicia. The course follows the northern Black Dome Trail and the Long Path from Acra Point, featuring approximately 15,000 feet of rugged, rocky, and steep c..

Many On The Genny is a 45-mile all-trail ultramarathon in Castile, New York, set inside Letchworth State Park’s famed gorge. The course runs on both sides of the gorge, featuring single-track, fields, footbridges, and bridle paths, delivering stunning vistas and challenging climbs. The event preserv..

The Run the Vineyards - Sheldrake Point Winery 5K takes place on Sunday, June 28, 2026, in Ovid, NY. The event is held at Sheldrake Point Winery, 7448 County Road 153, Ovid, NY 14521. Entry for the listed 5K event is shown as $45.52, including a $3.52 fee; the price is noted to increase after Octob..

RHSC's Super Hear-O 5K & Family Fun Day is an annual event held at Seneca Park - Wegman Lodge in Rochester, NY. It features a 5K road run/walk and a one-mile walk/roll/stroll, welcoming runners, walkers, rollers, and strollers of all ages. The event celebrates the efforts of RHSC heroes who support..

The Whiteface Mountain Races, held in Wilmington, NY, offer a challenging mountain running experience with some of the greatest vertical gain and loss per mile in the U.S. The event features multiple race options including a 21K (two loops), 10K (one loop), Vert Junky combo, 4K Ascent, and a 1-mile..

Parallel of Latitude 2025 is an 8-hour running event organized by the Finger Lakes Runners Club at Dryden Lake Park in Dryden, NY. The event uses a measured out-and-back course on the Jim Schug Trail. The course is described as flat and scenic. The out-and-back loop measures 3.45 miles. Participan..