Trail Running calendar near Roxbury 2026-2027

Late autumn weekend at Red Wing Recreation Area with looped 100k, 50k and 10k races over rugged, hilly trails. Expect big elevation, full aid, camping for 50k runners and finisher awards, with UTMB Index status for longer distances.

Run a scenic loop of single track and rolling farm trails at Gurski Farm in Brookfield, where the 4 mile course brings you past fellow competitors again and again. Choose 8 hour, 4 hour, 5K or 5K Canicross with medals and food.

Trail marathon and half marathon in Rockefeller State Preserve with start and finish at Rockwood Hall. Courses use wide, groomed carriage roads and offer run and walk options with charity bib entries.

Take on the Raven Rocks Run 10k through rocky climbs, ridgelines, ravines and hilly meadows at Ward Pound Ridge Reservation. This scenic but challenging trail route finishes by the old fire tower and closes out the Trail Mix series.

Tackle scenic but rugged trails at Tarrywile Park in Danbury with 10K, half and marathon options offering sweeping views of the park and lakes. Expect technical single track, steep climbs, finisher medals and hearty post race snacks.

Run the Storybook Half at Roosevelt Forest: a 13.1 mile trail of eight scenic loops on singletrack and doubletrack with roots, rocks, and rolling hills. Bring kids books to donate and earn a medallion and costume prizes.

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 Nov 28, 2026 at South Mountain Reservation in West Orange NJ offers 50K, 25K, 10K, 5K and a kids mile on a scenic 5K loop of mixed singletrack and carriage roads. Race supports Bigger Than The Trail.

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.

Join the Frosty Forest 5K on Saturday December 19, 2026 in Roosevelt Forest, Stratford CT for a festive off road trail run through snowy woods. Costumes welcome, awards for top finishers, and a commemorative finisher item for all.