Trail Running calendar near Cheshire 2026-2027

A repeated 3.3 mile out and back on the Tower Trail at Sleeping Giant State Park, with four hour and eight hour options and a cupless aid station at start and finish.

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.

A onesie-themed trail 5K at Ramapo Valley County Reservation featuring a flat, scenic loop around Scarlet Oak Pond and accessible course options.

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.

A 123 mile point to point ultramarathon from East Thompson to Southport, CT offering solo 200k and 100k options plus team relays. The mixed trail and road route has a 36 hour cutoff with staffed aid stations and medical support.

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.

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 mountain trail run in Ellenville, NY on April 24, 2027 offering a 25K (about 17 miles) and a 10 mile course across technical singletrack, cliffs and carriage roads, with aid stations and support for land conservation charity Run Wild, Inc..

A mountain trail event in the Shawangunk Ridge near Ellenville offering a 25K (closer to 17 miles) and a 10 Miler on technical singletrack and carriage roads, with significant climbing, marked courses, two aid stations, and proceeds support..