Trail Running calendar near Windsor 2026-2027

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.

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.

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 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.

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.

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.

Timed endurance running at Champs Campground in Whitehall NY on October 17 and 18, 2026. Choose a 6 hour, 12 hour, or 24 hour race on a flat 0.30 mile loop with aid station, camping, and limited fields.

Explore the scenic trails of 100 Acre Woods in Malta, New York. This community event on October 18, 2026 features 2k, 3k, and 5k trail runs. All proceeds support local trail maintenance.

A fall trail race at Mt. Tom State Park on October 24, 2026, with single and relay options from 5k to 25k on rugged single-track terrain. The event supports Kestrel Land Trust and includes aid stations, medical crews, and awards.

A community run at Ives Farm hosted by Cheshire Community YMCA and Cheshire Land Trust. Features a trail 5K, a youth Y Cup relay with elementary teams, a free Pumpkin Dash for young children and family fall activities.

A backyard ultramarathon and festival at Waters Farm in Sutton MA where runners complete a 4.167 mile loop each hour on the bell until one remains. The weekend features live music, hay rides, a kids fun run, farm tours, and local food.

A 4.9 mile mountain trail race in Keene, NH featuring four up and down laps on varied ski and single-track trails, with proceeds and food donations benefiting the Keene Community Kitchen.

A fall trail event in Harvard on October 25, 2026 featuring a 5K through orchard and woods plus a 1 mile kids fun run, with age divisions, awards, shirts, and proceeds benefiting the Harvard Conservation Trust.

A trail running event at Red Wing Recreation Area near Lagrangeville, NY, offering 100k, 50k and 10k looped courses with on-course aid, finisher medals and awards for top male and female finishers.

A trail half marathon at Moreau Lake State Park in Gansevoort, NY, covering roughly 14 miles with about 2,700 feet of elevation gain on technical singletrack. The course is fully marked with one aid station and parking at the park beach.

Timed trail event at Gurski Farm in Brookfield CT featuring an 8 hour race, a 4 hour option, and a 5K canicross on a 4 mile loop.

A 10K trail race in Penwood State Park featuring technical single track on the Metacomet Trail and rocky runnable terrain. No aid stations so runners must carry hydration for 6.2 miles; proceeds partly support NAMI.

Hugs From Vets Trail 10Kish in Henniker, New Hampshire on November 1 features a mixed trail and country road course and raises funds for American Legion Post 78. The field is limited to 150 participants and awards are given to overall and a..

A 5 mile trail race through varied terrain in Saratoga Spa State Park on November 1, 2026, with limited entries, age group awards, and post race drawings. Registration options include online pre-registration and cash or check on race day.