Trail Running calendar near East Hampton 2026-2027

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.

Rugged 5k trail run, ruck, or walk in Berkley MA on October 25, 2026 with in person and virtual options. Dogs may join on leash with a waiver and proceeds support The Baystate Beagle Club and Give2Those.org.

This fall trail run takes place at Powisset Farm in Dover, MA, featuring four scenic distances through farm and woodland trails. Post-race cider donuts and family activities like pumpkin painting add to the farm atmosphere. It's part of the..

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.

Experience a unique timed trail event at Gurski Farm featuring a four mile loop of rolling farm trails and single track. Choose between eight hour, four hour, or 5K options in a community focused environment.

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.

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.

Experience technical Northeast single track trails and 3000 feet of elevation at Tarrywile Park. Choose from 10K, Half Marathon, or Marathon distances featuring scenic lake views and a sustainable cupless environment.

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.

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.

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.

Challenge yourself on the historic Tower Trail at Sleeping Giant State Park. Choose between 4 or 8 hours to complete as many 3.3 mile loops as possible on this scenic gravel path to the Observation Tower.

Experience an exclusive trail run through the scenic Roosevelt Forest in Stratford. This 5K event features a natural off-road course limited to a small group of participants and includes custom finisher medallions.

Experience a winter trail challenge at Hale Education featuring 15 mile and 30 hour options. Navigate three unique loops through the Massachusetts woods while testing your endurance and self reliance in cold weather conditions.