Trail Running calendar near Chesterfield 2026-2027

We have found 127 Trailruns within 80 miles of Chesterfield. See below where and when you can find the races.

This 4-mile trail run in Schenectady Central Park uses a flexible time trial format. All proceeds support addiction recovery services, honoring a personal legacy. A pre race stretching session is included.

Trail races at Thacher State Park on August 23, 2026, with 10K, half marathon, marathon, and 50K options that share the same opening 10K loop. The event is cupless with multiple aid stations and race day packet pick up.

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 10 km race at Power Dam Recreation Area in Perkinsville, VT on August 30, 2026, part of the Western NH Trail Running Series. Online registration closes August 28, 2026; youth entries are free and age-based fees apply.

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.

September 2026

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..

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

The Cross-Connecticut Run for Mental Health Awareness will take place in Suffield on Saturday 12 September 2026. You can run 56 miles.

The Pisgah Mountain Trail Races will take place in Chesterfield on Sunday 13 September 2026. You can run between 23 and 50 kilometers.

A multi-day Spartan obstacle weekend at Killington Ski Resort on Sep 19 to 20, 2026, with Sprint, Beast, Ultra and kids races across steep off trail mountain terrain.

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.

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 features a 10K trail run, a 5K run/walk, and a 1-mile kids run at Shedd Park, with educational activities and proceeds supporting local conservation and environmental education.

A virtual 55K challenge linked to the Great Bay 5K in Stratham, New Hampshire. Complete 55 kilometers in one day or between October 1 and October 24, 2026; registration includes a shirt if ordered by October 1 and a bib with a beer or cider..

October 2026

A fall endurance event in Cohoes, NY offering 6 hour solo and relay, 3 hour and 1 hour timed formats, with buckles for solo runners over 26.2 miles, swag and finisher awards, and fundraising for Flutters of Hope Inc.

A 50 kilometer mountain ultramarathon around Lake George with roughly 9,000 feet of climbing, multiple aid stations, and required prior ultra-trail experience; the route starts and finishes at Camp Chingachgook in Kattskill Bay.

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