Trail Running calendar near Canton 2026-2027

A recurring one-hour trail run for women and nonbinary participants at North Reservoir in the Fells, covering a 3-mile loop at a conversational pace of about 11–12 minutes per mile. Sessions are in person and may be canceled for steady rain..

TARC Spring Classic in Weston, MA offers multiple running races on April 25, 2026, with distances from 10K to 50K. Registration is listed as free.

Experience three seasons of trail running and walking through scenic conservation land and a working vegetable farm in Wrentham with this unique 5K triple series.

Experience a scenic 5k trail run through conservation land and working farmland in Wrentham. Celebrate Earth Day with an off road course featuring natural obstacles and community focused agriculture support.

A student run community event on April 25, 2026 at MacDuffie School in Granby, MA featuring a flat cross country 5K and an optional Color Run, with 100% of proceeds going to Dakin Humane Society.

A professionally timed 5 km trail event around West Reservoir in Harwich on April 26, 2026, organized by Kiwanis of Lower Cape Cod with the Monomoy Key Club. Runners and walkers are welcome with an after run gathering at The Seal Pub.

A 12 mile technical out and back trail race on the Holyoke Range near Amherst, MA, with more than 3,500 ft of elevation gain. Rocky singletrack ridgelines, two manned water stations, and registration currently shows full with a waitlist.

A chip timed 5K trail race at Odiorne Point State Park with kids fun runs and a post race beach cleanup, raising funds for Marine Mammal Rescue.

The Big A 50K Trail Race is a challenging loop course on Mount Agamenticus with technical, rocky terrain and significant elevation. Participants can choose their distance, from 10 miles up to the full 50K. The event is free to register for,..

Celebrate National Truffle Day with a chocolate themed trail run at Giddings Park. This event features a three loop 5K for all ages and a kids fun run to support Franklin Elementary School programs.

Experience a trail run or walk through the campus of The Hartsbrook School in Hadley. Choose between a 5k or a 1 mile race on natural terrain while supporting local land stewardship and agricultural education programs.

Experience an all trail race through the scenic Frances A. Crane Wildlife Management Area. Choose between 10K, 20K, or 30K distances while supporting local wildlife and land conservation foundations.

A technical trail race on the Wapack Trail in Ashburnham, MA on May 9, 2026, offering 21.5, 43 and 50 mile options over rocky single track and significant elevation. Registration is limited, manually timed, and nonrefundable.

A trail race on Concord’s Winant Park Trails with two distances on singletrack, switchbacks, and nordic-style paths; proceeds benefit the Ralph Waldo Emerson School for Preschoolers and day-of-entry is available.

Trail races at Watuppa Reservation in Fall River on May 9, 2026, featuring grassy fire lanes, winding single track and aid stations each lap. Distances offered are 10K, 30K and 50K.

Trail running festival in Rollinsford, NH offering a 5 Miler, a 5K and a Canicross 5K on mixed rail trail and river single track, with specific rules for canicross teams and an aid station on the 5K route.

A spring 10K trail race on Block Island that mixes dirt roads, coastal tracks, rolling pastures and a steep double tiered climb near mile four. Packet pickup and registration take place at the Block Island School.

A community 5 km run and walk on May 9, 2026 at Pinkerton Academy in Derry, NH, with a course across campus and nearby cross-country trails. Proceeds support the Pinkerton Fund to benefit students.

A dog friendly 5K and a 2.6 mile walk at Borderland State Park on May 9, 2026 to benefit School on Wheels of Massachusetts. The event features refreshments, pup cups, kids pupsicles and free t shirts for early registrants.

A 50 mile point to point ultramarathon from Manchester, NH to Mount Monadnock with about 6000+ feet of gain over road, dirt road and trail. GPX only navigation, limited to 125 runners, with aid stations about every 10 miles.