Trail Running calendar near Cheshire 2026-2027

A 5 mile trail race at Muscoot Farm in Katonah, NY on October 25, 2026, with two kids races for specified age groups. Participants receive Farm Bucks for the farmers market; shirts are optional and ordered in advance.

The Fall Back Into The Trails Series returns to New York's Red Wing Recreation Area. Runners can tackle a 100k, 50k, or 10k on challenging, looped courses. All finishers earn a custom medal, and the ultras are UTMB Index races.

This 8-hour timed trail run takes place on the rolling farm trails at Gurski Farm in Brookfield, CT. Runners complete as many laps as possible on a course featuring single track. It offers a community atmosphere where participants frequentl..

Run through the historic carriage roads of the Rockefeller State Preserve in the Hudson Valley. The single-loop marathon and half marathon courses pass fields, stone walls, and scenic vistas without any pavement or cars. It's a walk-friendl..

The Raven Rocks Run is a 10k trail race through the scenic and hilly terrain of Ward Pound Ridge Reservation. The event also hosts a month-long virtual 100k walking, hiking, and running challenge. It supports the local park's friends group..

USATF Long Island hosts Open, Masters and Para Athletic cross country championships over an 8K course on November 8, 2026. Online registration is closed.

Experience a seasonal 5K trail run or walk through the scenic paths of Bethpage State Park. This family event features local refreshments and a welcoming atmosphere for participants of all abilities.

The Tarrywile Half Marathon challenges runners on technical, hilly trails in Connecticut's Tarrywile Park. With three distances available, the cupless event emphasizes trail respect and community. All finishers earn a unique medal.

A trail race at Burlingame State Park in Charlestown on November 15, 2026, offering 4-mile and 8-mile courses around Watchaug Pond. It is the first race in the WTAC fall trail series with multi-race registration discounts.

Run a storybook-themed half marathon on the trails of Roosevelt Forest in Connecticut. The course is an eight-loop journey through the woods, and costumes are encouraged. A book drive is also part of the event, supporting local children.

A Thanksgiving morning trail run supporting endometriosis research. Choose a run or walk on the 3.5-mile Mill Pond Trail, followed by complimentary yoga. All participants get a finisher medal and swag bag.

Celebrate the holiday at the Inwood Hill Turkey Trot 5K Run and Walk. This event offers a scenic course through Inwood Hill for participants of all abilities to enjoy a morning of fitness and community.

Enjoy a post holiday run or walk through the scenic trails of Bethpage State Park. Participants earn themed swag and enjoy refreshments from local partners at this festive 5K event.

Rob's Trail Run Edition stages 5K trail runs for adults and for high school or youth runners at Stillwell Woods Preserve in Woodbury, NY. The event supports The Center for Developmental Disabilities and is produced by RaceAwesome.

Experience a unique 5K trail run at Belmont Lake State Park where the focus is on luck rather than speed. Enjoy a chance to win cash prizes and refreshments at the finish line during this late November event.

The Tower Tag Challenge is a timed trail run in Connecticut's Sleeping Giant State Park. Runners complete 3.4-mile laps up and down the scenic Tower Trail within an 8-hour or 4-hour window. The event features awards, post-race refreshments,..

Run through Roosevelt Forest on a festive 5k trail course in Stratford. All finishers receive a custom medallion, and top runners earn awards. Holiday costumes are welcome for this charitable event.