Trail Running calendar near Bedford 2026-2027

Point-to-point trail races on the Wapack Trail offering 21.5, 43 and 50 mile options over rocky, technical terrain with significant elevation gain; five aid stations, manual timing, drop bag service, and a strict no-refund registration poli..

A trail race on Concord's Winant Park Trails with short (about 3.5 miles) and long (about 7 miles) courses. Proceeds benefit the Ralph Waldo Emerson School for Preschoolers in Concord, NH.

Trail running festival in Rollinsford NH along the Salmon Falls River, featuring a 5 Miler, 5K and Canicross 5K that mix rail trail, open fields and river single track.

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.

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.

Experience a scenic cross country trail run at Cole’s Family Farm in Maine. Choose between a 5K race, a ruck march, or a 1.25K fun run to support local youth honoring veteran history.

A 50-mile point to point ultramarathon from Manchester to Mount Monadnock with about 6000 feet of gain over roads, dirt roads and trails. The course is GPX only with minimal markings, five aid stations, and a 125-runner cap.

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.

New for 2026: an all-new Soapstone Mountain Half Marathon and a 6K Sampler in Stafford Springs, CT, both routed through Shenipsit Forest and past the Soapstone fire tower. The event is part of the Blue Blazed Trail Running Series and suppor..

A 25th annual cross country event in Newburyport, MA on May 17, 2026 with adult and youth 3 mile races plus a kids 1/2 mile. First 250 3 mile registrants receive shirts and race day donations support the Travis Landreth Scholarship Fund.

A community 5K through the PEA trails in Exeter plus kids fun runs in three age groups, post race music, food, raffles and awards. Free babysitting is provided for children of registered 5K participants.

A 5K Fun Run at Strongwater Farm in Tewksbury on May 17, 2026 to raise funds for programs supporting people with mobility challenges. The trail course crosses corn fields and woods, with a shorter accessible route and family activities on s..

A two-day 4K race on Cathleen Stone Island in Boston Harbor with individual and team entries, a short ferry ride, chip timing, and an on-island finish with dinner and beer. Funds raised support hands on science programs for Boston youth.

Trail races in Keene, NH using a 12.5K loop that can be repeated for 12.5K, 25K, 37.5K, or 50K. The course is technical single track and old jeep roads with aid stations, drop bag access, and portable toilets.