Trail Running calendar near Chester 2025-2026

The Raven Rocks 10k is an annual trail race held at the Ward Pound Ridge Reservation in Cross River, NY. Set against a scenic backdrop, the race features a challenging course that includes rocky climbs, ridgeline trails, and hilly meadows. The event not only promotes fitness and outdoor activity but..

The Li'l Rhody Runaround Trail Run is a popular running event taking place at Burlingame State Park in Charlestown, Rhode Island. Scheduled for November 16, 2025, the event features two race options: an 8-mile course and a 4-mile course, both set against the scenic backdrop of Watchaug Pond. This ra..

The Tarrywile Half Marathon is a challenging trail race set in Tarrywile Park, Danbury, Connecticut. Known for its tough terrain, the course features close to 3,000 feet of elevation gain and technical Northeast single track paths, offering stunning views of the surrounding area. Participants can ch..

The Baystate Dirty Dog Trail Run-Ruck-Walk 5k is a unique outdoor event held in Berkley, MA, designed to honor military personnel, first responders, and their K-9 companions. Participants can choose to run, ruck with weighted packs, or walk the rugged 5k trail, all while reflecting on the sacrifices..

The Tower Tag Challenge is a trail running event held at Sleeping Giant State Park in Connecticut, featuring a scenic course that ascends over 600 feet to the Observation Tower. Participants can choose between 4-hour and 8-hour options, completing loops on the Tower Trail, which includes a mix of cr..

The Frosty Forest 5K is an exciting trail running event taking place in Roosevelt Forest, Stratford, CT. Participants can run, jog, hike, or walk the 5K course while enjoying the beauty of nature and the festive holiday spirit. Costumes are encouraged, adding to the fun atmosphere.Awards will be giv..