Trail Running calendar near Woodbridge 2026-2027

A trail half marathon in Roosevelt Forest on November 21, 2026, run as eight 1.64 mile loops over singletrack and doubletrack with roots, rocks, and rolling hills. Costumes are encouraged and a book drive supports Books4Everyone.

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.

Squatchy Leftovers on November 28, 2026 at South Mountain Reservation in West Orange, NJ offers looped trail races from 5K to 50K on a mixed carriage road and singletrack course, supports Bigger Than The Trail, and includes family friendly..

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 race at Roosevelt Forest in Stratford, CT on December 19, 2026, run over two 1.55 mile loops. Holiday costumes are welcome, awards are given to top finishers, and all finishers receive a custom medallion; proceeds support local c..