Trail Running calendar near Winchendon 2026-2027

A 12 mile out and back trail race on the Holyoke Range in Amherst, MA with more than 3,500 ft of elevation gain on technical singletrack. Runners must carry their own water and two manned stations are provided.

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.

A 50K trail race at Mount Agamenticus featuring three roughly 10.35 mile loops, technical single track, rocks and roots, and about 5,787 feet of climb. Registration is free with a recommended donation to support Mount A Conservation.

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.

Multi distance trail races along the Wapack Trail from Mount Watatic to North Pack Mountain. The technical, rocky course has large elevation gain, five aid stations, drop bag service and limited entries.

Trail race on Winant Park Trails in Concord, NH offering approximately 3.9 mile and 7.0 mile routes. Proceeds support the Ralph Waldo Emerson School for Preschoolers and day of entry is available.

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.

A 5K trail run in Hanover New Hampshire held on Mother’s Day, featuring packed trails, open fields and mellow single track. Pre registration is online only and race day registration is available with different fees by age group.

A dirt road 50k in Leyden, Massachusetts on May 16, 2026, with 4,200 feet of elevation change and a course that passes through forests, fields, and an 1870s covered bridge. Registration closes May 13 and there is no race-day entry.

A 5 km cross-country event at Canterbury Shaker Village on May 16, 2026 with in-person and virtual options. Online registration closes May 15 at 12:00 noon ET and the registration fee is $25.

A May race day on the Ashuwillticook Rail Trail offering a marathon, half, 8K and kids mile, with race shirts, finisher medals, aid stations, and proceeds supporting trail maintenance.

Tails & Trails State Forest Run in Pittsfield State Park on May 16, 2026 features 50K, 25K and a 5 mile loop of single track, pine forests and mountain bike style trails while supporting local animal rescues.

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 an obstacle race on May 16, 2026 in Chester, New Hampshire, featuring a 5 km course run in multiple waves including a competitive wave. Online registration is closed and the event is limited to 800 participants.

Trail races at Soapstone Mountain in Stafford Springs, CT include a new half marathon and the Jerry Stage 6K Sampler. Courses run on the blue blazed Shenipsit Trail through Shenipsit Forest with on course aid for the half marathon.