Trail Running calendar near Windham 2026-2027

A community run at Shedd Park in Lowell offering a 5K, a 10K trail run, and a 1 mile kids loop, with trails, on-course support, family activities, and proceeds benefiting local conservation and education programs.

A 25 kilometer trail race through the Edwin L. Smith Preserve in Kennebunkport, Maine on October 3, 2026. Proceeds support the Kennebunkport Conservation Trust and registration is limited to 100 entrants.

A timed trail ultra in Cumberland RI offering 8 hour, 12 hour, and 34 hour options for individuals and teams up to four. The 4.2 mile loop mixes smooth trail and moderately technical rocky sections.

An annual 5K cross country run or walk in Franklin Park supporting Boston Latin School Athletics. Team registration is new for 2026 and fees are tiered with free entry for BLS students.

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 on the Nipmuck Trail in Ashford CT with varied terrain and wood bridges. Organizer Shenipsit Striders also offers a two person relay that splits the course into two halves.

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.

A one-mile community event in Gilford, New Hampshire on October 4, 2026, with categories for adults, youth, and children and a complimentary shirt for those who register before September 16.

Trail running at Tibbetts Field in Madbury includes a 5K and a 1 mile fun run over natural terrain through Powder Major Forest, with proceeds supporting youth recreation scholarships.

A 5K run and fitness walk at Highland Park in Attleboro on October 4 2026. The traffic free grass course uses two laps of a 1.55 mile loop and includes a kids 100 yard dash plus a virtual 5K option.

Trail races at Houghton's Pond in the DCR Blue Hills Reservation follow rolling dirt roads and forest paths with rocks and roots. Two distances are offered, about 7 miles and 3.7 miles, with notable elevation change on each course.

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.

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.

A community 5K and 1 mile fun run on October 11, 2026 supporting Unified programs at Beckwith and Dighton Middle Schools. Fees vary by registration period and registered runners receive T-shirts and awards for top finishers.

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.

Ghost Train Trail Races in Brookline NH on October 17 and 18 2026 features multiple trail events including a 30 hour ultramarathon and a haunted night 30 mile race. The course follows the historic Granite Town Rail Trail and supports local..

A six hour weighted trail race in Mansfield, MA where competitors carry and adjust weight each lap on a 2 1/2 mile out and back course; scoring uses pound miles called Kz to rank finishers.

United We Move Trailfest on October 17, 2026 at Fall River Bioreserve offers walk, run, and ride routes of varying lengths to support the Annual Campaign; routes are marked and GPX files are available.

Join a community trail race through the diverse terrain of Wompatuck State Park. Choose between a ten mile loop or a 50K distance on a course featuring rail trails and single track paths.