Trail Running calendar near Great Barrington 2026-2027

A community Thanksgiving trail event on 11/26/2026 at Mill Pond Way Trail with a 3.5 mile run or walk, chip timing, post race yoga for participants, free water and snacks, and proceeds benefiting endometriosis research.

A ninth annual charity 5K in Roxbury, Connecticut on November 26, 2026, with a 3.1 mile out-and-back course near Everett B. Hurlburt Community Park. Proceeds support local ambulance and scholarship funds and a food pantry collection.

Experience a 5K trail race through the scenic Stillwell Woods Preserve in Woodbury. This event honors the memory of Rob Lauterborn and supports the Center for Developmental Disabilities.

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.

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 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 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 point to point 123 mile ultramarathon across Connecticut on April 3, 2027, featuring trail and road sections, aid stations, five intermediate cutoffs and a 36 hour limit.

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.

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.

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..

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.

A 50 mile ultra, a 26.2 mile trail marathon, and relay options on the Shawangunk Ridge to raise funds for Mohonk Preserve.

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.