Trail Running calendar near Winsted 2025-2026

The Fall Back Into The Trails Series is an annual running event hosted by C.T.W Endurance at the Red Wing Recreation Area in Lagrangeville, NY. Scheduled for November 1-2, 2025, this event features three race options: a challenging 100k, a 50k, and a 10k, with varying elevation gains. The series is..

The "8 Hours at the Farm" event, organized by Steep Endurance, takes place at Gurski Farm/Williams Park in Brookfield, CT. This trail running event features a scenic 4-mile loop with a mix of single track and rolling farm trails, fostering a vibrant community atmosphere among participants. Runners c..

The Pocantico Hills Marathon, taking place in Rockefeller State Park, offers both a marathon and a half marathon on scenic, rolling courses with stunning views of the Hudson River and Palisades. Participants will enjoy a picturesque route featuring fields, stone walls, lakes, and forests. This event..

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 Tarrywile Half Marathon, scheduled for November 16, 2025, is a challenging trail race set in Danbury, Connecticut. Known for its tough terrain, the course features significant elevation changes and technical single-track paths, offering stunning views of the surrounding area. Participants can ch..

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..

The Tower Tag Challenge is a trail running event held at Sleeping Giant State Park in Connecticut, known for its stunning views and diverse trails. Participants can choose between 4-hour and 8-hour options, racing up and down the Tower Trail, which ascends over 600 feet to the Observation Tower. Eac..

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..