Trail Running calendar near Canterbury 2026-2027

Trail event in Pittsfield, Vermont, May 6 to 9, 2026, offering distances from 10 miles to 200 miles through the Green Mountain National Forest. Team entries can secure the same start time and service member discounts are available.

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 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 spring trail running and walking series at Great Glen Trails in Gorham, NH running May 14 to June 18, 2026. Courses of 5 km, 3 km and 1.5 km are offered, with series and one time entry fees and leashed dogs permitted.

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.

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.

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.

A six-race trail series across Oxford Hills preserves from May to October, with each course about 3.1 Miles. Season preregistration is $72, single races $15, and student races are $5 each.

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.

Experience Maine's premier trail running festival featuring races from 5K to 100K. This multi day event includes a 30 hour endurance challenge, dog friendly canicross races, and a sunset run at Pineland Farms.