Trail Running calendar near Darien 2026-2027

Experience Long Islands scenic Robert Moses Causeway in this multi day running event. Support local veterans while choosing between marathon, half marathon, 10k, and 5k distances with finisher medals for all participants.

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 technical trails and peak fall foliage of Harriman State Park at this mountain trail event. Choose between a half marathon or 10 km course featuring steep climbs and scenic Hudson Valley views.

This Halloween-themed run on New Jersey's legendary Clinton Road offers a spooky adventure. Participants can choose from a Zombie Crawl, a 5k, or a 10k, all featuring zombie volunteers and a festive finish line celebration.

An off road 50k through interconnected woodland preserves in southern Connecticut, featuring rolling forest roads and rocky single track. The event is nonprofit and proceeds support local land conservation, with volunteer roles for aid stat..

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.

Experience an obstacle course race at Sunflower Valley Farm featuring 5K and 10K distances alongside kids races. Conquer muddy trails and creek runs in the New York countryside this autumn.

Trail races at Red Wing Recreation Area in Lagrangeville, NY offering 100k, 50k and 10k looped courses with significant elevation. The 50k and 100k hold UTMB Index status and provide aid stations plus finisher medals.

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.

A trail 10k at Ward Pound Ridge Reservation plus a November virtual 100k challenge, with race results, photos, and a custom finisher woodallion for 100k finishers.

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

Trail races of 50 mile, 50K and a half marathon traverse Staten Island trails and support the Greenbelt Conservancy. Courses use loop formats with multiple aid stations and specified crew and pacer locations.

Experience the diverse terrain of South Mountain Reservation with a looped trail race offering 5K, 10K, and half marathon distances. Enjoy a mix of single track and fire roads with support provided at regular aid stations.

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.

Trail race at Tarrywile Park in Danbury, CT, offering Marathon, Half Marathon and 10K on technical, hilly single-track trails with finisher medals, podium awards and a $600 half-marathon time bonus.

A trail half marathon in Roosevelt Forest using eight 1.64 mile loops to total 13.1 miles. The event includes pavilion aid each loop, a book drive with Books4Everyone, costume prizes, podium awards, and participant swag.

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.

The FEAR Trail Fest is a 5-mile trail race on the scenic Yellow Trail in New Jersey's Lewis Morris Park. With a runnable mix of rocks, roots, and climbs, it welcomes everyone from first-timers to veterans. The event focuses on sustainabilit..

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.