Trail Running calendar near Great Barrington 2026-2027

Technical trail races in Burlington CT on the Tunxis Trail offering 8K and 5K courses that pass the CT State Trout Hatchery and Nassahegan State Forest.

A trail running event in Gardiner, NY offering a 5 km run, an optional 10 km two-lap route and a 200 yard kids run, with pre registration T shirt incentives and a sneaker recycling program.

Experience an ultimate endurance test at Mohawk Mountain by taking on 61 miles and 29,155 feet of elevation gain. Participants have 72 hours to run hike or walk their way to an Everest sized vertical achievement.

A 24 hour Backyard Ultra trail event at Mohawk Mountain Ski Area in Cornwall, CT, featuring about 14,400' of elevation and options to run, hike or walk.

A 30-hour trail ultra at Roosevelt Forest in Stratford CT with 2.5-mile loops, buckles at 100 miles, and a 50 participant field limit.

Timed endurance event in Cohoes, NY on Oct 3, 2026 with 1 hour, 3 hour and 6 hour solo and relay options supporting Flutters of Hope.

A 26.4 mile trail marathon in Ashford, CT on October 4, 2026 with rugged terrain and a two-person relay option.

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.

A fall trail race day in Norfolk, CT offering 5K, 10K and a half marathon with steep climbs, private-trail sections, a cupless policy with water stations, and on-site food and beverage vendors.

Trail half-marathon in Cold Spring NY on October 4, 2026 featuring 13.7 miles and 4,000 ft of gain through the Hudson Highlands; proceeds support NYNJTC.

On 10/10/2026 the Gemstone Sparkle Sprint 5k at Gemstone Farm in Wilton CT features a timed trail 5k, an accessible stroller run, live music, food and access to the farm, with proceeds supporting The Prospector's mission.

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.

Experience a scenic 5K run on the historic carriage roads of Rockefeller State Park Preserve. Support trail maintenance while enjoying autumn views of Swan Lake and rolling pastures.

Trail running at Mohawk Mountain Ski Area with 5K, 10K, half and marathon routes on ski slopes and state forest, cupless aid stations and finisher medals.

A pickle-themed Halloween obstacle event in Wallkill, NY with an adult 5K and a 1K kids course, themed medals, costumes, mud, and a community-focused Donate a Dragon 3D printing project.

A time-based event in New Salem MA offering 12 hour and 24 hour run or walk options around the town common on October 11, 2026.

A 5K race at Veeder Tree Farm in Earlton, NY on October 11, 2026, with proceeds benefiting the Leukemia and Lymphoma Society.

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 3.5 mile trail run and walk on the scenic, flat Mill Pond Trail at Woodtick Recreation in Wolcott CT on October 17, 2026. Tiered online registration is available and a post-event meal is included with registration.