Trail Running calendar near New Boston 2026-2027

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 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.

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.

Trail event in Bradford Vermont with looped mountain course, 30 hour, 12 hour and 6 mile options, tarot themed awards and a 100 runner cap.

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..

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 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.

Trail event in Brookline, NH with multiple races on the Granite Town Rail Trail and proceeds supporting local conservation.

Mountain up-and-down race at Cranmore Mountain in North Conway offering 10 km and 5 km options, USATF sanctioned and $7,500 in prize money for 2026.

A 6 hour weighted trail race in Mansfield MA where lap distance is multiplied by the weight carried to produce Kz on an out and back course of at least 2.5 miles.

A 4.1 miles trail race in Ravenswood Park, Gloucester, held October 18, 2026, as part of the North Shore Trail Series. The course uses single-track and carriage roads, with online registration closing October 15 and race-day registration av..

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.