Trail Running calendar near Windham 2026-2027

Portland's only backyard ultra takes place on the scenic Back Cove Trail. Runners test their endurance by completing a 4.167-mile loop every hour until only one remains. The flat gravel course features full support and a unique last-runner-..

A technical 5.6-mile loop trail race in Northfield, NH, run over six laps with a ten-hour limit and about 4,400 feet of elevation gain; the event supports Spaulding Academy & Family Services and provides aid stations and drop bags each lap.

The TARC Blue Hills Skyline Trail Run will take place in Canton on Saturday 11 July 2026. You can run 12 kilometers.

Join a community trail run or walk at Owen Bell Park to support the Ryan French Memorial Scholarship Fund. This family friendly event features a 5K trail, a walk, and a free kids fun run.

The Kingman Farm Trail Race is an old-school, show up and race event over 3.8 miles of rolling nordic paths and switchback singletrack. It benefits the Doug Flutie, Jr. Foundation for Autism. Day-of registration is available.

A three-day stage race around Lake Sunapee covering 75 miles with ~15,500 ft gain, plus a 50k option. The format includes overnight camping, organizer gear transport, stocked aid stations, mandatory safety gear, and a $30,000 prize purse.

Experience an obstacle course with over a dozen mud pits at the 508 INTL Adventure Sports Center. Enjoy a non competitive environment featuring music, food, and a festive atmosphere for both participants and spectators.

The Tarc Summer Classic will take place in Medfield on Saturday 8 August 2026. You can run between 10 and 40 miles.

The 5K Race to the Ledges will take place in Concord on Saturday 8 August 2026. You can run 5 kilometers.

Trust Trail Fest offers 5k and 10k races on forest trails at the Kennebunkport Conservation Trust headquarters, followed by music, food, a beer tent and family activities. Proceeds support the Trust in Education programs.

Experience a scenic off-road trail run or walk through the conservation lands of White Barn Farm. This cup-less 5k event supports local sustainable agriculture and community food security in Wrentham.

A 4.61 mile trail race at Moody Park in Claremont NH featuring narrow single track, wet sections and a steep drop and climb at Gravity Cavity. The event is part of the Western NH Trail Running Series and benefits the local parks department.

Experience a scenic trail run through Vineyard Hill Reservation and Bradley Palmer State Park. Choose between 5 km and 10 km distances on a rolling course featuring wide trails and the open landscapes of Shaw Field.

Experience a classic 5k cross country race through the scenic fields of Waters Farm in Sutton. Join the USATF New England Grand Prix season opener on a spike friendly course with both open and masters divisions.

A scenic 10 km trail loop in Perkinsville Vermont that passes three dams and includes a low river crossing with a rope and lifeguard. Post-run refreshments and a nearby swimming hole are available at the finish.

Traverse the scenic ski slopes and forest trails of Wachusett Mountain in this timed event featuring loops from 7 to 28 miles. Earn a finisher medal within 10 hours and enjoy a post trek party at the mountain base.

The TARC Fall Classic will take place in Carlisle on Saturday 5 September 2026. You can run between 10 and 50 miles.

Experience a flat and non technical trail race at Cherry Hill Farm in Gorham Maine. Choose between 50k 25k or 10k distances consisting of multiple loops around the scenic farm property.

The Veterans Count Nashua 5k Fun Run & Walk will take place in Nashua on Saturday 5 September 2026. You can run 5 kilometers.

The DownForTrailRunning will take place in Newfield on Saturday 5 September 2026. You can run between 5 and 20 kilometers.