Trail Running calendar near Hauppauge 2026-2027

A trail series at Red Wing Recreation Area offering 100k, 50k and 10k on multi-loop courses with notable elevation. The 50k and 100k are UTMB Index races and all finishers receive custom 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 race on Staten Island offering 50 mile, 50K and half marathon looped courses through Blood Root Valley, High Rock Park and La Tourette Park. Proceeds benefit the Greenbelt Conservancy and routes include multiple aid stations.

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 races at Tarrywile Park in Danbury offering Marathon, Half Marathon and 10K on technical, hilly single-track with substantial elevation; finisher medals, podium awards and cash bonuses for fast half marathoners.

A 13.1 mile trail race in Roosevelt Forest made up of eight laps of a 1.64 mile wooded loop, featuring on course aid, a book drive with Books4Everyone, costume prizes, participant medallions, and podium awards for top finishers.

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.

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.

Experience a diverse 5K loop course at South Mountain Reservation featuring carriage trails and technical singletrack. Choose from distances ranging from a Kid's 1M to a 50K in this community focused trail event.

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 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.

A mid-December trail event at Holmdel Park offering about 50 km and a halfish option over repeated 4.65 mile laps on mostly trail terrain. Proceeds support MissionCleanWater's clean water projects.

Trail 5K in Roosevelt Forest, Stratford CT on Dec 19, 2026. Participants can run, jog, hike or walk and may wear holiday costumes; awards go to the three fastest men and women and a portion of proceeds supports local causes.