Trail Running calendar near North Fork 2026-2027

An ultramarathon in Prospect Park, Brooklyn on December 6, 2026 offering 50K and 50 mile looped courses with potluck-style aid, Skratch Labs hydration, chip timing, and finisher belt buckles.

A weekend trail event in Blydenburgh County Park featuring a Backyard Ultra with 4.167 mile hourly loops and a separate 4.16 mile lapping race. A portion of proceeds supports the Long Island Greenbelt Trail Conference.

Experience an exclusive trail run through the scenic Roosevelt Forest in Stratford. This 5K event features a natural off-road course limited to a small group of participants and includes custom finisher medallions.

Chip timed 5k run and walk at Osprey’s Dominion Vineyards in Peconic, NY on March 20, 2027, over a two lap cross country loop with a postrace wine pour for eligible participants. Registration includes a T shirt, collapsible wine glass and f..

A six-hour trail ultra at Roosevelt Forest featuring a 2.3-mile loop with 191 feet of climb per lap, chip-timed laps, on-course aid and food, podium awards, medallions for over four hours, and a limited field supporting local charities.

A late-March trail event at Bethpage State Park offering a 5K trail run, a free kiddie fun run, race shirt, on-site refreshments and a virtual participation option.

A 16 mile out-and-back trail race on the Nipmuck Trail near Bigelow Hollow State Park in Union CT with technical terrain, minimal aid, and proceeds supporting local trails.

A community 5K run and free kiddie run at Bethpage State Park with trail terrain, a virtual option, and donations benefiting the Never Stop Running Foundation.

Trail races on a 25K loop at Sleeping Giant State Park featuring technical singletrack, steep rock scrambles, and an optional second loop for the 50K.

A community trail event in Cross River, NY featuring a hilly wooded 5K, a 4K walk through the main trail, and a 200 m kids dash on the contest track. Registration opens 8/24/2026 with limited pre-registration t-shirt incentives.

A 5K trail run and walk at Blydenburgh County Park in Smithtown, NY on mixed surfaces through park trails. The event supports Last Chance Animal Rescue and includes onsite hydration, restrooms, same day results and photos.

Looped trail races of 17K and 50K at Penwood State Park, featuring rocky single track on the Metacomet Trail and a nine hour cutoff for the 50K.

Shore2Shore in East Islip, NY on April 17, 2027 follows the Greenbelt from north shore to south shore and offers 50K and 25K distances.

Women and non-binary runners take on 5K, 10K, or a timed 4 hour loop on the trails around Lake Mohegan in Fairfield, CT.

A spring 10K trail race in Cross River NY on April 25 2027, organized by Leatherman's Loop Races. Entry is by lottery with registration Jan 8 to Jan 11 2027 and the $58 fee includes the park entry.

VCP 50K is a looped trail ultramarathon in Van Cortlandt Park on 01 May 2027. The 50K course starts with a flats lap then ten cross country loops, with stocked aid stations, drop bag access, finisher medal, singlet, meal and beer.

Camp Mountain Laurel offers a family color run plus a 5K trail run and 5K trail walk at Hamden/North Haven YMCA and New Haven YMCA Youth Center on May 8, 2027; registration opens Feb 19 and first 100 pre-registrants receive a giveaway.

A nine hour timed trail ultra on a 2.2 mile loop through Roosevelt Forest in Stratford, CT. Entry is limited to 50 participants and awards go to the runners with the most miles by the race end.

A trail 5K at Blydenburgh County Park in Hauppauge with on site refreshments, an in person and a virtual participation option, and proceeds benefiting the Never Stop Running Foundation.

A 5 mile trail race at Muscoot Farm on May 23, 2027 with two kids races on farm trails. The event is organized by Run the Farm Races and is sanctioned by USA Track and Field.