Trail Running calendar near Hebron 2026-2027

Take on the Mohawk Mountain Race at Mohawk Mountain Ski Resort with marathon, half marathon, 10K and 5K on challenging ski mountain trails featuring sweeping fall foliage and plenty of climbs and descents. Finishers earn medals and enjoy po..

Join the 20th Wayland / HFC Striders Cross Country Festival on October 11, 2026, featuring youth 3K races and open 5K events that support Wayland High School cross country and track. Presented by Middlesex Savings Bank with awards and commu..

Enjoy a scenic 3 mile trail at Sakonnet Vineyard, then celebrate with wine, dinner, music and a souvenir wine glass. BBQ only and kids BBQ options are available for those who prefer to skip the run.

A point to point trail race along the Air Line Trail State Park between Willimantic and Putnam, CT. Events include marathon, marathon relay teams, half marathon, 10K and TackleJR, with proceeds supporting local students.

The Grills Trail Run will take place in Misquamicut on Saturday 24 October 2026. You can run between 10 and 10 miles.

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.

Timed trail event at Gurski Farm in Brookfield, CT featuring 8 hour and 4 hour continuous loop races plus 5K and 5K canicross. The course uses single track and farm trails and includes finisher medals, awards, food, and beverage options.

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.

Trail races at Tarrywile Park near Danbury offering 10K, half marathon and marathon distances with technical single track, substantial elevation and lake views.

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, Stratford, run as eight laps of a 1.64 mile wooded loop with roots, rocks and rolling hills. The event features a children’s book drive, costume prizes, a finisher medallion and on-course aid.

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.

A 5K trail run through Roosevelt Forest in Stratford, CT on December 19, 2026, with awards for the top three men and women and a custom finisher medallion. A portion of proceeds supports local charities.