Trail Running calendar near Westport 2026-2027

A one mile obstacle course in Warren, RI with two giant mud pits, kids play area, food and giveaways. Proceeds support Thrive Outside and its programs to expand youth access to nature.

Experience the technical terrain of Cockaponsett State Forest with 4 and 9 mile trail races. Navigate hills and rocky paths in Chester to support PanCAN and the Blue Blazed Trail Race series.

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

A women only 5K obstacle mud run at Carter & Stevens Farm in Barre, MA on September 20, 2026. The course has 18+ obstacles, welcomes participants ages seven and up, and emphasizes teamwork over competition.

A trail event on the Moosup Valley State Park Trail featuring 5K, 8K, 10K and a Kids Fun Run. Parking and the finish are at Weidele's Pizza with post-race food, awards and a medallion or shirt option.

A community 5K at Goddard Park in Warwick on September 26, 2026, featuring fields and wooded trails along Greenwich Bay, on-site parking, T-shirts, and awards.

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.

A community run at Shedd Park on September 27, 2026, featuring a 5K run or walk, a 10K trail run, and a 1 mile kids fun run to support local conservation and education programs.

Trail races at Bradford Preserve on October 3, 2026 feature 5K, 10K and a free kids run on dirt trails with seasonal course markings and a required orange clothing rule per state regulations.

A 5K fall trail run and walk at Ryan Park in North Kingstown on October 3, 2026, benefiting the North Kingstown Firefighters Association. Registrations before September 14 include a race day t shirt and top finishers receive medals.

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

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.

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 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.