Trail Running calendar near Irvington 2026-2027

A 30 hour looped trail ultra at Roosevelt Forest in Stratford, CT, run on a 2.23 mile lap with roots, rocks and a notable hill. Multiple distances are offered and awards are based on most miles completed during the time limit.

Run through 300 acres of scenic vineyards on a flat trail course in Peconic. Enjoy live music, food trucks, and a post-race glass of wine at this chip-timed autumn event.

Experience the wooded trails of Irvington during this four mile race. Navigate a course featuring elevation changes and natural turns through the local forest landscape.

A multi-day trail event near Rocky Point, NY, run on a 10.48-mile loop with distance options from 10 miles to 150 miles. Two staffed aid stations provide food and volunteer support; pacers and crews are allowed with prior notice.

A trail 5K and 1 mile accessible run in Wilton, CT on 10/10/2026 with participant T-shirts, on-site food and entertainment, spectator options, and sponsor levels; proceeds support the Prospectors mission for employment opportunities.

Experience a premier 13.1 mile trail race through the woods of New Rochelle. This half marathon takes runners across local trails for a focused off road experience in New York.

Run or walk through the scenic trails of Blydenburgh Park this autumn. Participants enjoy a 5K trail course complete with seasonal treats and commemorative event swag.

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..

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.

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.

Celebrate the tenth anniversary of this event with an 8K or 5K trail run through Unionville Vineyards. Enjoy live music and a glass of wine at the post race reception in Ringoes.

Fall Back is the autumn edition at Jacobsburg State Park on November 8th 2026, run on a roughly 5 mile loop of single track and gravel. Options include a single 5 mile loop or laps within 3 hour and 6 hour timed formats.