Trail Running calendar near Columbia Point, Boston 2026-2027

A 26.4 miles trail marathon in Ashford Connecticut on October 4, 2026, run on the Nipmuck Trail with rocky and rooty sections and wood bridges. A two person relay is offered and cutoffs are set by elapsed times.

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 5K trail race and 1-mile fun run at Tibbetts Field in Madbury, NH on October 4, 2026, featuring a 2-mile loop through Powder Major Forest over natural terrain. A portion of proceeds will support a local family in need.

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.

A beach fun run at Sandy Neck Beach in Barnstable offering 3K and 5K courses on sand; organized by the MSOA to raise funds for scholarships for high school seniors and partnered with local groups for 2026.

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 six-hour weighted trail race in Mansfield, MA where runners complete laps of about 2.5 miles, carry variable weight per lap, and score pound-miles called Kz; the highest total Kz in each division wins.

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.

A fall trail event at Grills Preserve in Westerly with 10 mile and 10 km courses across single-track trails and riverfront sections. Club timing is used, orange clothing is required, and post-race refreshments are provided.

A harvest-season 5K trail event at White Barn Farm in Wrentham with off-road terrain, a midway water station, bib pick-up the day before, family Harvestween activities, and a portion of registrations donated to the local food pantry.

A 5K on October 24, 2026 at Stratham Hill Park that runs along Great Bay and benefits Great Bay Stewards; the mostly downhill course includes a race shirt for timely registrants and a bib with a beer or cider coupon.

A trail event at Camp Greenough offering a 5K loop, a 10K two-loop option, and a six hour endurance challenge. Participants may run or ruck with specified weight standards and complete as many closed-course loops as they choose.

A 4.9 mile mountain trail race in Keene, NH on October 25, featuring four up and down laps on different trails, 1650 feet of elevation, prize money and age group awards, with proceeds supporting the Keene Community Kitchen.