Trail Running calendar near Windham 2026-2027

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 backyard style ultramarathon at Kate Furbish Preserve East in Brunswick, Maine where runners complete 4.17 mile laps each hour up to a 12 hour, 50 mile limit. $20 fee; nutrition is not provided and proceeds after expenses go to Preble Str..

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 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 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 community 5K in Bethel, ME presented by HealthReach Community Health Centers to support after school programs for K-12 students. The event has an in person race on May 16 and a virtual option May 1 to May 16; under 18 entries are free.

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 muddy trail event of roughly 13.1 miles around Jericho State Park in Berlin NH that is open to trail runners this year as well as mountain bikers. Proceeds support Coös Cycling Club trail maintenance and youth cycling programs.

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 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.

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.

Run of The Fellowship is an in-person trail event at Clifford Park in Biddeford, Maine on May 30, 2026. It offers a 5K route and a longer full quest option, welcomes costumes, and is pending final permits and insurance.

A 23K mountain trail race in Tamworth NH with roughly 4,800 feet of climbing, a technical loop over the 3,478 foot summit of Mount Chocorua, mandatory mountain safety gear, and inclusion in the White Mountain Endurance Cup.

A six mile trail race at Bradbury Mountain in Pownal, Maine that begins the Bradbury Mountain Trail Race Series. The course follows single and double track trails with rolling hills and a race cutoff of 1 hour 48 minutes.

A 5.4 mile trail race through Dogtown in Rockport and Gloucester, MA featuring varied terrain and named historic trails. Runners and walkers are welcome; early registrants receive T-shirts and prizes are awarded by overall and age categorie..