Trail Running Calendar Massachusetts 2026-2027

Experience a scenic trail run through Vineyard Hill Reservation and Bradley Palmer State Park. Choose between 5 km and 10 km distances on a rolling course featuring wide trails and the open landscapes of Shaw Field.

A 5K cross country race at Waters Farm in Sutton Massachusetts that opens the USATF New England XC Grand Prix series. Separate men's and women's open races, on site registration, and a post race awards ceremony.

An inclusive trail festival at Northfield Mountain on August 29, 2026 that centers queer and trans runners and allies. It offers a 20k prediction race, an untimed 5k fun run or hike, and a Kid's Run with community-focused prizes.

Timed loop trails on Wachusett Mountain with 7, 14, 21, and 28 mile options over ski slopes and single-track. Participants have 10 hours to finish, with weighted vest options and marked courses; finishers receive a shirt and patch.

Trail Animals Running Club hosts a multi distance trail event at Great Brook Farm State Park on September 5, 2026. Looped 10K and 10 mile courses cover distances from 10K to 50 miles, plus a youth fun run and a Yeti Mischief Mile.

A 5K trail run and a 1/4 mile kids fun run at Felix Neck Wildlife Sanctuary in Edgartown, MA, with scenic trails and birdlife. Proceeds benefit the sanctuary's wildlife protection, education, and conservation programs.

Trail races in Pittsfield State Forest on September 12, 2026 feature 50K, 25K, 15K and 5 mile options. The double loop course includes long climbs, fast descents and three aid stations, with proceeds supporting Free to Run.

A USATF New England Cross Country Grand Prix meet at Great Brook Farm Ski Touring Center in Carlisle, MA on September 13, 2026, featuring a youth 2K and several 5K races across open and masters categories.

The Arc'teryx Run Boston will take place in Milton on Sunday 20 September 2026. You can run 10 kilometers.

Trail races at the Assabet River National Wildlife Refuge in Sudbury MA include a 10K, a 30K and a 6 hour timed event. The course uses dirt and gravel double track trails with two aid stations and cupless fueling.

Run for Nature in Lowell on September 27, 2026 features a 10K trail run, a 5K run or walk and a kids one mile fun run, with marked trails and community activities supporting local conservation and education.

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.

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.

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 beach fun run at Sandy Neck Beach in Barnstable with 3K and 5K sand courses where participants walk, run, or crawl. Proceeds support MSOA scholarships for marine biology students and a partner scholarship effort in 2026.

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 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.