Trail Running calendar near Brattleboro 2026-2027

A multisport festival at Pawtuckaway State Park offering swim, bike and run options for people who identify as women. Choose an individual triathlon, two sport combo, single sport or a relay team in a non competitive setting.

A trail-based 5K obstacle course at Wasserman Park on September 26, 2026, featuring 12+ beginner to intermediate obstacles. Entry is limited to 200 participants, costs $40, and early registrants receive a race shirt and finisher medal.

Trail races in Burlington CT organized by the Burlington Land Trust as a fundraiser. Courses on the Tunxis Trail cover mixed terrain and visit landmarks such as the CT State Trout Hatchery, Nassahegan State Forest, and Devil’s Kitchen.

A weekend of mountain bike and ultra running at Ascutney Outdoors near West Windsor offering 50 mile and 50 km races, relay options, and kids fun races. Proceeds benefit Vermont Adaptive and event information includes aid stations and campi..

Trail races at the Assabet River National Wildlife Refuge in Sudbury MA include a 10K, a 30K and a 6 hour timed event. The course uses dirt and gravel double track trails with two aid stations and cupless fueling.

A community run at Shedd Park on September 27, 2026, featuring a 5K run or walk, a 10K trail run, and a 1 mile kids fun run to support local conservation and education programs.

A timed endurance event in Cohoes, NY offering 6-hour, 3-hour and 1-hour solo options plus 6-hour relays, organized by Flutters of Hope Inc to raise awareness and funds for people affected by eating disorders.

A 50 kilometer trail ultramarathon on October 3, 2026 in Kattskill bay, NY, starting and finishing at Camp Chingachgook with about 9,000 feet of climbing across multiple Lake George peaks. Prior ultra-trail experience is required.

Trail races in Groton, Massachusetts on October 4, 2026, organized by local running and trails groups. Two distances, 9.5 miles and 3.4 miles, total entries limited to 250, online registration closes October 3.

A 26.4-mile trail marathon in Ashford, CT, on the Nipmuck Trail featuring rocks, roots, mud, and wood bridges, with a two-person relay option and race shirts available before September 12.

Keene Family YMCA Fall Foliage Trail Races feature 5K and 10K trail courses starting and finishing at the Keene YMCA, with chip timing, age-group prizes, and proceeds supporting YMCA programs and access.

Join the annual Run Stanley event at Stanley Park for a variety of trail races including a 5K K9 run and an accessible 1 mile stroll. Support local wildlife sanctuary maintenance while enjoying a community day in the park.

The Haystack Mountain Challenge on October 4, 2026, features a 5K, 10K and a half marathon across Barbour Woods and Haystack Mountain, with steep climbs, private trail sections, a cupless policy, water stations and on site refreshments.

Experience the peak of New England autumn on a journey through the mountains and fields of central Massachusetts. This trail event offers three distances crossing state borders for runners seeking adventure on the Midstate Trail.

A community run on October 10, 2026, organized by the Lebanon Recreation, Arts, and Parks Department, following the Rail Trail from Enfield along Mascoma Lake and the Mascoma River to a finish in Lebanon. Fees change before race week and pa..

Community 5K and a 0.5 mile youth run at Pitney Meadows Community Farm on October 10, 2026. The mixed surface, spectator friendly course runs on grass and stone dust and raises funds for the farm's programs.

On October 11, 2026 the HFC Striders Cross Country Festival returns to Wayland for its 20th running, featuring 3K youth races across age groups and two 5K open races, with awards and proceeds benefiting Wayland High School.

A rugged trail race at Pawtuckaway State Park featuring technical terrain, boulders, streams and a rocky climb. It offers a half marathon and a 5 mile option and lists $7500 in prize money for 2026.

Experience a point to point trail race in Northeast Connecticut on the Airline Trail. Choose between marathon, half marathon, and 10K distances with individual or relay team options to support local student education.

A multi format trail event on the Granite Town Rail Trail in Brookline and Milford NH on October 17 and 18 2026, featuring 7.5 mile relays, 15 mile and 30 mile races and a 30 hour ultramarathon. Proceeds support local trail conservation.