Trail Running calendar near Waterbury 2026-2027

A multi-race weekend in Bay Shore, NY featuring marathon, half marathon, 10K, 5K, kids runs and a virtual challenge, with race days October 17 and 18, 2026 and fundraising for local veterans.

Point to point trail race in Northeast Connecticut on October 17, 2026, running through the Air Line Trail State Park from Willimantic to Putnam. Offers marathon, half marathon, 10K, and a marathon relay with proceeds supporting local stude..

The Tom Centinaro Memorial "Dam" Race will take place in Waterbury on Saturday 17 October 2026. You can run 4 miles.

A technical trail half marathon and 10K in Harriman State Park near Tuxedo, NY on October 18, 2026, featuring steep climbs, rocky singletrack, marked routes, aid stations, and a five hour finish cutoff.

Run Clinton Road with volunteer zombies and themed aid stations for a spooky, fun challenge this October. Choose a Zombie Crawl, 5k or 10k and celebrate at the finish line festival with music, a costume contest and a Survivor Medal for all..

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

A 5 mile trail race at Muscoot Farm in Katonah with two kids races by age group, Farm Bucks for the farmer's market, optional shirts, and no dogs permitted except trained service dogs.

A weekend trail event at Red Wing Recreation Area in Lagrangeville, NY offering 10K, 50K and 100K loop races with continuous aid, finisher medals, and UTMB Index designation for the 50K and 100K.

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.

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.

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.

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 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.