Trail Running calendar near Shandaken 2025-2026

The Raven Rocks 10k Run is an annual trail race held at Ward Pound Ridge Reservation in Cross River, NY. Known for its challenging course, the race features rocky climbs, ridgeline trails, hilly meadows, ravines, and the historic fire tower site, offering scenic views of Long Island Sound, Connectic..

The Tarrywile Half Marathon, held at Tarrywile Park in Danbury, Connecticut, is known as one of the toughest trail half marathons in the region. The challenging course features nearly 3,000 feet of elevation gain and technical Northeast single-track terrain. Runners enjoy stunning views of Danbury a..

The Roxbury Thanksgiving Day Charity Race is a 5K event held annually in Roxbury, Connecticut. Scheduled for Thanksgiving Day, November 27, 2025, the race takes place at the Everett B. Hurlburt Community Park located at 18 Apple Lane.Participants run a 3.1-mile course through the scenic park setting..

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..

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..

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..

Wawayanda Trail Fest is a challenging trail running event held in Vernon Township, New Jersey, at Wawayanda State Park. The festival offers multiple race distances including a 100K, 50 Mile, 50K, and Half Marathon, featuring a unique 26+ mile loop course with scenic rhododendron tunnels, marsh bridg..

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 Jack Bristol Lake Waramaug Ultra Races, held in Kent, Connecticut, is a historic ultra running event featuring 100K, 50-mile, and 50K distances. The course consists of rolling loops primarily on flat, paved roads around scenic Lake Waramaug, known for personal record performances. Runners enjoy..

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..

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. Set on the ski slopes and trails of Plattekill Mountain, the race offers a rigorous mountain challenge ideal for athletes seeking to test their limit..