Trail Running calendar near Derry 2026-2027

A recurring morning trail run in the Fells for women and nonbinary folks. The group runs a 3 miles loop at a comfortable pace of about 11 to 12 minutes per mile; steady rain or thunder cancels.

On May 2-3, 2026 White Lake Ultras run at White Lake State Park in Tamworth NH. Runners complete a slightly technical 2 mile single track loop with a short beach section and choose from 24 hour, 12 hour, or 6 hour formats.

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,..

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 chip-timed trail 5K plus 1-mile fun and walk events at Whitaker Woods on May 9, 2026, run on wooded single and double track with varied terrain. Proceeds benefit White Mountain Community Health Center.

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.

The Free Spirit 50K is a scenic ultra on the dirt roads of Leyden, Massachusetts. The route passes historic farms, forests, and a vintage covered bridge, offering a classic New England countryside experience.

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.

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 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.