Trail Running calendar near Red Hook 2026-2027

A technical trail event at Tarrywile Park in Danbury offering 10K, half marathon and marathon distances with significant elevation gain; finisher medals, podium awards, and post-race food are provided.

A 13.1 miles trail race in Roosevelt Forest, Stratford, run as eight 1.64 miles loops on marked singletrack and doubletrack. The event features a children's book drive, costume prizes, participant medallions and podium awards for top finish..

Join the Soul n Body Thanksgiving Trail Run in Wolcott CT for a spirited 3.5 mile loop around Mill Pond Way, complete with finisher medals, swag and post race yoga. Proceeds benefit endometriosis research and furry friends are welcome.

Hit the trails at Rob's Trail Run Edition in Woodbury on Sunday, November 29, 2026. Choose a 5K for adults or youth and enjoy scenic singletrack through Stillwell Woods Preserve.

A timed out and back event on the Tower Trail at Sleeping Giant State Park where runners repeat roughly 3.3 mile laps to the Observation Tower in four hour or eight hour formats. Aid is at the start and finish and the race follows a cupless..

A 5K trail event at Roosevelt Forest in Stratford on December 19, 2026. Holiday costumes are allowed, awards go to the top three men and women, and all finishers receive a commemorative medallion. The field is limited and registration is fi..