Trail Running calendar near Woburn 2026-2027

An all-trail event on the Moosup Valley State Park Trail in Moosup, CT offering 5K, 8K, 10K and a free Kids Fun Run with post-race shirts or medallions and food at Weidele's; proceeds benefit a local Rotary charity.

Trail races and a six hour timed event take place on double track dirt and gravel trails at Assabet River National Wildlife Refuge in Sudbury MA. The race is cupless, aid stations are provided, and pacers are allowed for the six hour event.

A community run at Shedd Park featuring a 5K, a 10K trail run, and a 1-mile kids fun run, with educational displays and proceeds supporting LP&CT's conservation and education programs.

Survival of the F.I.T.test is a 30 hour trail ultra held in October as part of the F.I.T. Challenge calendar in Cumberland, Rhode Island. Results for past editions are published online after each race.

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 25K trail race at the Edwin L. Smith Preserve in Kennebunkport, Maine on October 3, 2026, with proceeds to the Kennebunkport Conservation Trust. Registration is limited to 100 entrants and includes a shirt if registered by September 5.

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 on Connecticut's Nipmuck Trail featuring rocks, roots, mud and wood bridges, plus a two-runner relay option. The course uses a 13 mile segment with out-and-back sections and published cutoffs.

Experience the seasonal scenery of New Hampshire at the Keene Family YMCA Fall Foliage Trail Race. Choose between a fast 5K or a 10K with elevation gain to support local community programs.

A one-mile charity run at Gunstock Mountain Resort on October 4, 2026, benefiting Big Brothers Big Sisters of New Hampshire & Vermont. Online registration closes October 2; adult and teen entries are $20, children under 12 enter free.

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.

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.

Join the 20th Wayland / HFC Striders Cross Country Festival on October 11, 2026, featuring youth 3K races and open 5K events that support Wayland High School cross country and track. Presented by Middlesex Savings Bank with awards and commu..

A technical, rugged trail race at Pawtuckaway State Park offering a half marathon and a five mile course. New for 2026 the event features $7,500 in prize money and multiple aid stations on rocky, forested terrain.

A community running event at the Dighton Rehoboth High School cross country course on October 11, 2026 offering a 5K and a 1 Mile Fun Run with shirts and awards, benefiting Beckwith Middle School athletics.

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.

Ghost Train Rail Trail Race on October 17–18, 2026 offers races from 7.5 miles to a 30-hour ultramarathon along the Granite Town Rail Trail, with proceeds supporting Brookline and Milford conservation efforts.

A six hour weighted lap race on Mansfield's WWII Veterans Memorial Trail where competitors carry chosen weight each lap and earn Kz by multiplying measured weight by lap distance; the highest 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.