Trail Running calendar near Charlton 2026-2027

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 the Nipmuck Trail featuring rocks, roots, mud, and wood bridges, with a two-person relay option and race shirts available before September 12.

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.

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 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.

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 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.

A 3 mile trail run through Sakonnet Vineyard in Little Compton followed by dinner, wine and music among the vines. Race entry includes timing, a t shirt and a souvenir wine glass; dinner only options are also available.

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.

A six hour weighted trail race in Mansfield, MA on October 17, 2026 where runners complete as many 2.5 mile out-and-back laps as they can, scoring pound-miles called Kz by multiplying lap distance by the weight carried.

United We Move Trailfest at Fall River Bioreserve on October 17, 2026 offers walk, run, and bike routes to support the United Way annual campaign.

An off road 50K through interconnected woodlands near Guilford CT on October 18, 2026, featuring rocky single track and rolling forest roads for experienced trail runners.

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.