Trail Running calendar near West Hartford 2026-2027

Run or walk through the scenic trails of Blydenburgh Park this autumn. Participants enjoy a 5K trail course complete with seasonal treats and commemorative event swag.

Experience a point to point trail race in Northeast Connecticut on the Airline Trail. Choose between marathon, half marathon, and 10K distances with individual or relay team options to support local student education.

This 3.5-mile trail run/walk on the flat Mill Pond Trail happens in Wolcott, CT. The Wolcott Lions Club hosts the event, which includes a race t-shirt and clam chowder. Registration opens online with a lower early-bird rate.

Experience the diverse landscapes of Westerly and Hopkinton in this trail race series event. Runners can choose between 10K and 10 mile distances featuring riverfront views and technical single track paths.

Run a scenic autumn 5k trail through Wrentham conservation land and a working farm. This cup-less race supports local agriculture and includes family Halloween fun. It's the final event of the Farm to Trail 5K Series.

Experience peak autumn foliage at the Mt. Tom Trail Race featuring a 25k solo or relay, a 10k, and a 5k fun run through rugged Massachusetts state park trails with significant elevation.

Experience a unique trail race through the forests and meadows of Muscoot Farm. Enjoy distances for all ages followed by a visit to the local farmers market with your farm buck vouchers.

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..

Experience a single loop marathon or half marathon on historic carriage roads in the Rockefeller State Preserve. Enjoy views of the Hudson River and stone bridges on a course with no pavement or cars.

Test your endurance at this backyard ultra in Winchendon featuring a 4.1666 mile loop through fields and trails. Choose from the last runner standing format, timed races, or a single lap challenge in a relaxed community setting.

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..

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.

Experience a magical 13.1 mile trail race through the rolling hills of Roosevelt Forest. Complete eight loops of a wooded course while supporting a children's book drive in this unique costume friendly event.

Test your endurance at YMCA Camp Sloper with a 400 minute timed challenge or a 4 mile trail race. Explore rolling wooded trails in Southington while supporting local charities and youth running programs.

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.

Experience a 5K trail race through the scenic Stillwell Woods Preserve in Woodbury. This event honors the memory of Rob Lauterborn and supports the Center for Developmental Disabilities.

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,..