Trail Running calendar near Fairfield 2025-2026

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 Squatchy Leftovers Trail Race, taking place on November 29, 2025, at South Mountain Reservation in West Orange, NJ, offers a variety of distances including 5K, 10K, 25K, and 50K. This family-friendly event supports the non-profit organization Bigger Than The Trail, which provides cost-free thera..

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, 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 is approximately 3.4..

The Frosty Forest 5K is an exciting trail running event set in the scenic Roosevelt Forest in Stratford, United States. 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.Awa..