Trail Running calendar near Windham 2026-2027

A lakeside trail run in Goshen, New Hampshire on September 5, 2026, with 3 mile and 5.7 mile courses, awards, swag, and a raffle. The longer distance awards points in the Western NH Trail Running Series.

Trail races at Bear Brook State Park on September 12, 2026 featuring a Half Marathon and a variable ultramarathon between 50k and 100k, GPX only navigation and no cup aid stations.

Experience the summit of Mount Agamenticus with a 5K or 1 mile trail race. Support local conservation efforts while running or hiking through Maine trails and participate in a raffle for all entrants.

Experience a scenic run through wooded conservation trails finishing at the Hooksett Public Library. This community event features a 5K trail race and a half mile kids fun run to support local youth programs.

A community 5K in Hillsborough, NH on September 20, 2026, organized by the Hillsboro Fire Department. The off-road course may be uneven and strollers are not recommended; registration runs March 25 to September 19 with a $30 fee.

A trail event in Arundel, Maine on September 26, 2026 featuring 5k, 10k and half marathon routes through the ACT and Eastern Trails. All entrants receive a medal and a t shirt, and there is a free kids bike race.

Experience an endurance tradition at Mt. Ascutney featuring 50 mile and 50 km ultra runs, mountain bike races, and team relays. This scenic event supports Vermont Adaptive and includes fun races for kids.

Trail races and a six hour timed event take place on double track dirt and gravel trails at Assabet River National Wildlife Refuge in Sudbury MA. The race is cupless, aid stations are provided, and pacers are allowed for the six hour event.

Run for Nature in Lowell features a 10K trail run, a 5K run/walk, and a 1-mile kids run at Shedd Park, with educational activities and proceeds supporting local conservation and environmental education.

A virtual 55K challenge linked to the Great Bay 5K in Stratham, New Hampshire. Complete 55 kilometers in one day or between October 1 and October 24, 2026; registration includes a shirt if ordered by October 1 and a bib with a beer or cider..

Experience the Bobcat Ridge 25K trail race at the Edwin L Smith Preserve in Maine. This event features a limited field of 100 runners and supports the Kennebunkport Conservation Trust.

Run the winding single lane trails of Groton Town Forest with a choice of 9.5 mile or 3.4 mile courses featuring roots, rocks and rolling climbs. Limited to 250 runners, this community race supports Groton trail maintenance and finishes wit..

Experience an old school trail race along the historic Nipmuck Trail in Connecticut. This 26.4 mile double out and back event follows the blue blazed trails through challenging New England terrain.

Experience the seasonal scenery of New Hampshire at the Keene Family YMCA Fall Foliage Trail Race. Choose between a fast 5K or a 10K with elevation gain to support local community programs.

The Mile for Mentoring will take place in Gilford on Sunday 4 October 2026.

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.

Join the 20th Wayland / HFC Striders Cross Country Festival on October 11, 2026, featuring youth 3K races and open 5K events that support Wayland High School cross country and track. Presented by Middlesex Savings Bank with awards and commu..

Vulcan's Fury Trail Race at Pawtuckaway State Park offers a half marathon and a 5 Miler over technical trails with boulder fields, switchbacks, stream crossings and a rocky ridge called the Devil's Staircase. Three aid stations support runn..

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.

Experience New Hampshire’s original 30 hour ultramarathon on the historic Granite Town Rail Trail. Choose from multiple distances and relay options in this flat and fast Halloween themed fundraiser for local trail conservation.