Trail Running calendar near Greenfield 2026-2027

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.

Trail races in Waterville Valley, New Hampshire with multiple distances including a 50K with 7,700 feet of climbing around nearby 4,000 foot peaks. Courses start and finish at Town Square and the event is cupless.

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.

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.

A lakeside trail run in Goshen, New Hampshire on September 5, 2026, with 3 mile and 5.7 mile courses, awards, swag, and a raffle. The longer distance awards points in the Western NH Trail Running Series.

Trail races at Bear Brook State Park on September 12, 2026 featuring a Half Marathon and a variable ultramarathon between 50k and 100k, GPX only navigation and no cup aid stations.

A three-day Scottish heritage festival at Loon Mountain Resort in mid September featuring music, Highland Dance, heavy athletics, sheep dog trials, seminars and family programming.

Test your limits at the birthplace of Spartan Race in the Green Mountains of Vermont. Choose from distances ranging from 5km to 50km featuring steep climbs and rugged off trail descents at the iconic Killington Ski Resort.

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.

A community 5K in Hillsborough, NH on September 20, 2026, organized by the Hillsboro Fire Department. The off-road course may be uneven and strollers are not recommended; registration runs March 25 to September 19 with a $30 fee.

A trail event in Arundel, Maine on September 26, 2026 featuring 5k, 10k and half marathon routes through the ACT and Eastern Trails. All entrants receive a medal and a t shirt, and there is a free kids bike race.

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.