Trail Running calendar near Jaffrey 2026-2027

A community fundraiser in Pomfret Center with a trail 5K and a 0.5 mile kids run supporting the Pomfret Community School PTO. Early and later registration fees differ and awards plus finisher medals are given.

A community 5K in Jaffrey, New Hampshire on September 19, 2026, offering two course options: a mixed woods trail and a straight rail trail. Proceeds benefit the Jaffrey Firefighters Company Inc.

Pair up for a three hour endurance relay on a two mile loop of trails and fields. Alternate laps with your partner to accumulate the maximum distance possible in this team based challenge.

A community 5K in Hillsborough, NH on September 20, 2026, organized by the Hillsboro Fire Department. The off-road course may be uneven and strollers are not recommended; registration runs March 25 to September 19 with a $30 fee.

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

A multisport festival for people who identify as women at Pawtuckaway State Park on September 26, 2026, offering triathlon, two sport, single sport and relay options on supported swim, trail bike and trail run courses.

A weekend of endurance mountain biking and trail ultrarunning at Ascutney Outdoors in West Windsor Vermont, offering 50 mile and 50 km solo races, multiple relay formats, and kids fun races. Proceeds support Vermont Adaptive.

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.

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.