Trail Running calendar near East Islip 2026-2027

Looped trail race in South Mountain Reservation offering 11M, 20M, 50K and 50M over three marked loops with varied terrain and on-site aid.

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 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.

A mountain trail event at Harriman State Park near Bear Mountain on April 3, 2027 offering 10K, 10K ruck and 13.1M courses on rugged, technical singletrack with marked routes, aid stations, rucking divisions, and adaptive support.

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.

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

Two days of mountain obstacle racing at Mountain Creek Resort featuring Sprint, Super, Beast, Ultra and kids races across steep terrain.

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

Off-road triathlon, paddle tri, duathlon, mountain bike races and trail runs at Stokes State Forest with USAT-sanctioned multisport formats and world-series trail qualifiers.

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 technical trail event near Beacon, NY offering a roughly 14.5 mile half and a 26.5 mile full with large elevation gain, exposed climbs, staffed aid stations, post race food, a shirt and a finisher item.

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 5K run/walk through Bethpage State Park featuring soft trails, live timing, free finish-line photos, and advance bib pickup at Orangetheory Fitness Farmingdale.

A technical mountain trail race in northern New Jersey offering a 50K with over 7000 ft gain plus 10 mile and 5 mile options, map requirements for the 50K, mandatory gear checks, and aid stations on the longer courses.