Trail Running calendar near South Orange 2026-2027

Trail and 5K races at Hillside Park on October 18, 2026, benefit a free mammography program. A kids fun run for ages 5 to 12 is included, with chili and vegetarian food and timing by Compuscore.

A community 5K run and 1 mile fun dash at Fenton Lane Park in Chesterfield on October 18, 2026, supporting local charities. The event includes race shirts, custom medals for top finishers, post race refreshments and posted results.

A trail ultramarathon at Washington Crossing Park on October 24, 2026, offering 25K+ and 50K courses across historic, technical singletrack with multiple aid stations and finisher swag.

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 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.

Experience an off-road race weekend at Yeager’s Farm & Market featuring 4 and 10 mile trail runs. Enjoy a local atmosphere with post-race beer and bagels and earn a unique long sleeve tech shirt.

A trail 8K and 5K at Unionville Vineyards on November 8, 2026 with chip timing, live results, onsite music, post race wine, and awards. Walkers and children are welcome and the event includes water stations and post race amenities.

A trail event at Jacobsburg State Park on a roughly five mile loop of single track and gravel. Runners do one loop or repeat for three or six hour time limits; spring and fall editions use opposite directions.

A trail and gravel running event in Wissahickon Valley Park offering 10 km, 10 mile and half marathon options with chip timing, aid stations, limited field size, and a post-race party with live music and warm food.

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 charity trail event at Hillside Park on November 8, 2026, offering 10 km and 5 km races to benefit a free digital mammography program, with race timing, age-group medals and participant T-shirts.

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.