Trail Running calendar near Mount Kisco 2025-2026

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 Spring SOMO Timed Trail Races take place at South Mountain Reservation in South Orange, New Jersey. This event features a looped trail course of 1.88 miles (just over 3K) that includes single track, pavement, and fire road sections. Runners can choose from multiple race options: 1 loop (3K), 2 l..

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..

The Wawayanda Trail Fest is a challenging trail running event held in Vernon Township, New Jersey, at Wawayanda State Park. It features multiple distances including a 100K, 50 Mile, 50K, and Half Marathon, all running on a scenic 26+ mile loop course with rhododendron tunnels, marsh bridges, gravel..

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 Jack Bristol Lake Waramaug Ultra Races, held in Kent, Connecticut, is a historic ultra running event celebrating its 52nd anniversary in 2026. It features three race distances: 100K, 50 miles, and 50K, all conducted on primarily flat, rolling loops around scenic Lake Waramaug on paved roads. The..

XTERRA New Jersey is an off-road multisport event held at the scenic Wawayanda State Park, featuring over 40 miles of trails and a clear lake. Part of the XTERRA World Tour, it offers a variety of races including trail runs (5K to 42K), gravel and mountain bike races, and triathlons such as full dis..

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, 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..

3 Days at the Fair is a multi-day ultrarunning event held at the Sussex County Fairgrounds in Augusta, New Jersey. The race features a certified 1-mile flat loop course composed of pavement and crushed gravel, suitable for various distances including 6, 12, 24, 48, 72, and 144-hour races, as well as..

Run The Farm is a popular trail running event held at Muscoot Farm in Katonah/Somers, New York. The race series features a 5-mile trail run along scenic paths showcasing the natural beauty of the working farm and surrounding parkland. The event includes two kids' trail races tailored for different a..

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..

Pinky’s Rock n Rolla is a unique 4-mile trail race held in Richmond Hill, New York, offering runners an authentic trail running experience on natural hiking trails rather than typical bridle paths or gravel roads. The course, located in Forest Park, features naturally carved terrain shaped by glacia..