Trail Running calendar near Islip 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.

A 3.5 mile trail run and walk on the scenic, flat Mill Pond Trail at Woodtick Recreation in Wolcott CT on October 17, 2026. Tiered online registration is available and a post-event meal is included with registration.

A fall trail running event at Harriman State Park on October 18, 2026 offering a technical **13.1M** and a hilly **10K**, with marked singletrack, two aid stations for the half, a five hour finish cutoff, and limited field size.

A Halloween themed event on Clinton Road in West Milford, NJ offering a 1 mile Zombie Crawl plus 5k and 10k races. The course features zombie volunteers, themed aid stations, and a finish line festival with awards and a costume contest.

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..

A fall trail event at Muscoot Farm in Katonah on October 25, 2026 featuring a five mile trail race and two kids races. Participants receive Farm Bucks for the farmer's market and shirts are available by preorder.

A 5K Run / Walk and Kids Fun Run at Hallock State Park on October 25, 2026, with a virtual 5K option. Proceeds support the Long Island Greenway and include a post-race wine crawl with vendor specials for participants 21 and over.

A weekend Spartan obstacle event at Sunflower Valley Farm on October 31 and November 1, 2026 featuring Sprint, Super, Kids races and Hurricane Heat formats across woods, mud and creek runs, with spectator access and medals for finishers.

Experience the Fall Back Into The Trails Series at Red Wing Recreation Area in Lagrangeville. Choose from 100k, 50k, or 10k distances featuring a loop course with elevation gain. This UTMB Index event offers medals and awards.

A timed trail event at Gurski Farm on a 4 mile loop of single track and farm trails. Options include an 8 hour race, a 4 hour race and a 5K plus 5K canicross; the event is cupless with aid at start finish.

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 running event at Ward Pound Ridge Reservation with a ten kilometer race and a November 100 kilometer virtual challenge. The course features rocky climbs, ridgeline views, and a custom finisher woodallion for challenge completers.

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

A charity 5K run, 1 mile walk and virtual 5K on November 8, 2026 in Central Park of Morris County to raise funds for housing stability organized by Family Promise of Morris County.

A multi-loop trail event on Staten Island offering a half marathon, 50K, and 50-mile courses that pass through Blood Root Valley, High Rock Park, and La Tourette Park, with proceeds supporting the Greenbelt Conservancy.

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, CT offering 10K, half and marathon on technical single track with significant elevation. Finisher medals, awards and a cash bonus for fast half marathoners.

A trail half marathon in Roosevelt Forest featuring eight laps of a 1.64 mile wooded loop with roots, rocks, and rolling terrain. The event includes a book drive, costume prizes, event swag, and podium awards for top finishers.

Trail races at YMCA Camp Sloper in Southington CT feature a timed 400 minute loop event and a 4 mile two lap race on a roughly two mile wooded course. The event includes an aid station, chip timing, and finisher medals.