Trail Running calendar near Avon 2026-2027

Join a scenic trail run through NE Connecticut along the Air Line State Park Trail with marathon, half, 10K, relay and junior distances. Tackle the Trail supports local students pursuing higher education.

Discover scenic single track trails at Grills Preserve in Westerly on October 24, 2026 with 10 mile and 10K options. Choose a distance and enjoy riverfront views and bridges as race two of the WTAC Fall Trail Race Series.

Join FALL Run The Farm on October 25, 2026 at Muscoot Farm in Katonah for a scenic 5 mile trail race plus kids races for ages 2 to 12. Finish with farm market treats and a festive family friendly fall vibe.

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.

Pocantico Hills Races at Rockwood Hall in Tarrytown on November 7, 2026 feature marathon and half marathon loop courses on wide carriage roads. Expect rolling climbs, Hudson River and Palisades views, fields, forests and car free trails.

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.

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.

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.

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.