Trail Running calendar near Chesterfield 2025-2026
We have found 57 Trailruns within 80 miles of Chesterfield. See below where and when you can find the races.
We have found 57 Trailruns within 80 miles of Chesterfield. See below where and when you can find the races.
Moreau Half is a scenic, challenging 14 mile trail race around Moreau Lake State Park on November 1, 2025. Expect technical singletrack, big climbs and a true backcountry feel for a rewarding day on the trails.
The Hugs from Vets Trail will take place in Henniker on Sunday 2 November 2025. You can run 10 kilometers.
Challenge yourself in the Saratoga Stryders Fall Back 5 Mile Trail at Saratoga Spa State Park, featuring rolling ridges, single track, grassy stretches and a stair climb. Enjoy a scenic, challenging course and post race prizes.
Push your limits at Race for DFL, a backyard ultra at Kenty's Farm in Winchendon MA where runners repeat 4.1666 mile laps until only one remains. Choose 6, 12 or 24 hour options and enjoy themed laps, fun gear and great camaraderie.
Join the Dave Driscoll 19th Annual Age Before Beauty 5K cross country at White Memorial in Litchfield on Sunday, November 9, 2025. Enjoy a scenic all cross country course as the first race of the day ahead of the Junior Olympics.
Test your grit at the Mount Ascutney Vertical Backyard, a Last Person Standing uphill race in Brownsville VT where runners repeat hourly laps of steep ascent until only one remains. Aid, indoor facilities and camping are available.
Tackle an accurately measured 8K cross country course through the MDC Reservoir Complex in West Hartford on Sunday, November 23, 2025. Rolling gravel and trail terrain with a touch of pavement make this a scenic challenge for all paces.
Join the 27th annual Novemberfest Race, a scenic 4 mile through Mine Falls Park to benefit the Nashua Children's Home. Finish at Martha's Exchange for a lively post race party, raffle and beer proceeds supporting the cause.
Join the Roxbury Thanksgiving Charity Race, a scenic 5K in Roxbury, Connecticut, starting and finishing at Everett B. Hurlburt Community Park. Run or walk to celebrate the season and support local causes.
Join a scenic road and rail trail run with prizes for top finishers. Route may change for weather and the event will be canceled if it snows. Entry is donation based; proceeds benefit a local dog rescue and community theater.