Trail Running calendar near Chester 2026-2027

A trail race in Windham, Maine on August 22, 2026 offering 13M, marathon and 50K on technical single track trails. The event supports local trail organizations through participant donations and event proceeds.

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.

Trail races in Waterville Valley, NH offering a 50K with about 7,700 feet of climbing, a 23K on historic trails, a 4 mile forest route, and a 1 mile fun run. The 50K requires mandatory mountain gear and the event is cupless.

A scenic *10 km* loop at the Power Dam Recreation Area in Perkinsville, VT, with grassy trails, dirt roads and a calf-deep river crossing secured by a rope and lifeguard. The event benefits Springfield High School Cross Country and finishes..

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.

Join the Trail Animals Fall Classic at Great Brook Farm for scenic trails and distances from youth fun runs to 50 mile ultras. Community vibe, limited spots, and on course aid make this a favorite, so bring your own hydration and register e..

A looped trail event at Cherry Hill Farm in Gorham, ME, offering 50K, 25K and a 10K trail race on a flat, nontechnical course with one aid station and on-course lap support.

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

Experience an untimed trail run through the woods of western Maine featuring 3.6 mile laps of forest roads and single track. Enjoy on site camping and wood fired pizza along the scenic shores of Mirror Lake.

Trail races at Bear Brook State Park include a half marathon and a variable ultramarathon distance between 50k and 100k. The event is GPX navigated with no cup service at aid stations so runners must carry their own water.

A pair of technical trail races at Echo Lake State Park near North Conway offering a 5 mile course on Cathedral and Whitehorse Ledges and a half marathon that adds a Red Ridge loop and significant vertical gain. Part of the 2026 Skyrunner U..

Experience a historic celebration of Scottish heritage at Loon Mountain Resort featuring heavy athletics, stone lifting, and traditional music amidst New Hampshire's scenic fall foliage.

Experience the summit of Mount Agamenticus with a 5K or 1 mile trail race. Support local conservation efforts while running or hiking through Maine trails and participate in a raffle for all entrants.

Experience a scenic run through wooded conservation trails finishing at the Hooksett Public Library. This community event features a 5K trail race and a half mile kids fun run to support local youth programs.

Experience the natural beauty of Maine by running or walking through woodland trails in Arundel. This conservation focused event offers 5k, 10k, and half marathon distances along with a kids bike race and live music.

Experience an endurance tradition at Mt. Ascutney featuring 50 mile and 50 km ultra runs, mountain bike races, and team relays. This scenic event supports Vermont Adaptive and includes fun races for kids.

Trail races and a six hour timed event take place on double track dirt and gravel trails at Assabet River National Wildlife Refuge in Sudbury MA. The race is cupless, aid stations are provided, and pacers are allowed for the six hour event.

Run for Nature in Lowell on September 27, 2026 offers a 10K trail run, a 5K run or walk, and a 1 mile kids fun run while supporting the Lowell Parks and Conservation Trust with educational activities and light refreshments.

Experience a scenic downhill course along the shores of Great Bay or take on the virtual 55K challenge. Support local estuary conservation while enjoying a community race that includes a long sleeve shirt and a post race beverage.