Trail Running calendar near Wading River 2026-2027

Timed trail event at Gurski Farm in Brookfield CT featuring continuous 4 mile loops for 8 hour and 4 hour runners plus new 5K and 5K Canicross options. Post race food and beverages are provided.

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.

A trail 10k at Ward Pound Ridge Reservation paired with a November virtual 100k challenge that rewards finishers with a custom engraved woodallion; the race uses rocky ridgeline trails and includes an on-course water stop near the fire towe..

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.

Enjoy scenic trails around Watchaug Pond at the Li'l Rhody Runaround on November 15, 2026, with 8 mile and 4 mile course options. Part of the WTAC Fall Trail Race Series, it welcomes runners of all levels.

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..