Trail Running calendar near Guilford 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 Tower Tag Challenge is a trail running event held at the iconic Sleeping Giant State Park in Hamden, Connecticut. The race features a simple yet demanding course on the Tower Trail, a mostly smooth carriage road that ascends over 600 feet in 1.5 miles to the park's Observation Tower, offering st..

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 Frosty Forest 5K is a trail running event held in Roosevelt Forest, Stratford, Connecticut. This 5K race offers participants a chance to escape the road and enjoy a scenic course through nature. Runners, joggers, hikers, and walkers are welcome, with a recommendation for some trail experience.Pa..

The Squatchy Onesie Fest 5K is a fun and unique trail running event held at Ramapo Valley County Reservation in Mahwah, New Jersey. Participants are encouraged to wear their favorite onesies, adding a playful atmosphere to this winter race. The course is a scenic, mostly flat "lollipop" loop around..

The Sleeping Giant Trail Runs, held at Sleeping Giant State Park in Hamden, Connecticut, is a challenging trail running event known as one of the toughest in the Northeast. The race offers two distances: a 25K loop with over 3,000 feet of vertical gain and a 50K option consisting of two loops. The c..

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 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..

Leatherman's Loop is a popular 10k trail race held annually in spring at Ward Pound Ridge Reservation in Cross River, New York. The event features a challenging and scenic trail course through the reservation's natural terrain. Due to high demand, entry is determined by a lottery system.The race is..

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..

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..

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..