Trail Running calendar near Ipswich 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..

Prospect Acres 8 hour ultra on April 18, 2026 features repeated 2 mile loops through fields and woods with 230 ft of elevation gain per lap. Free parking, sauna and cold plunges are available and registration costs $25.

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 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,..

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 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.

The Canterbury Shaker Village XC 5k will take place in Canterbury on Saturday 16 May 2026. You can run 5 kilometers.

Cross country 5K at Cole's Family Farm in Dayton on May 16, 2026 supporting the Southern Maine Young Marines. Options include a 1.25K fun run and a 5K ruck march; entry includes a patriotic t-shirt and participation medal.

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.

Run or walk a 5k on the Southern New England Trunkline Trail in Franklin. This event supports the development of an abandoned rail bed into a multi use path connecting local communities.

Celebrate the eighth annual Trillium Spring 5K in Canton or participate virtually from anywhere. Join over 500 runners at the brewery to support Girls on the Run Greater Boston with races for adults and children.

Wason Pond Wrangler is a family friendly obstacle course trail race around Wason Pond in Chester, New Hampshire with a *5K* route and more than ten obstacles. The event raises funds for local nonprofits and welcomes individuals and teams.