Trail Running calendar near Chesterfield 2026-2027
We have found 115 Trailruns within 80 miles of Chesterfield. See below where and when you can find the races.
We have found 115 Trailruns within 80 miles of Chesterfield. See below where and when you can find the races.
Experience an authentic off road adventure in Guilford with a 10k trail loop featuring technical single track paths and rock scrambles through Westwoods to support local land conservation.
A weekly Northampton cross country series held April through August on an accurately measured 5 km course through fields and woods. Day of registration is required, with modest fees and a season pass option.
Experience an obstacle course race in Cumberland featuring a 3.2 mile loop with 1000 feet of elevation. Choose from competitive waves, multilap options, or a signature 12 hour ultra endurance challenge.
Run a unique quarter marathon distance on the paved trails of West Hartford Reservoir. This chip timed 6.55 mile race features a two loop course with post race treats and age group awards.
A USATF certified point to point half marathon in Albany featuring a mostly downhill paved route along the Helderberg Hudson Rail Trail, six aid stations, live tracking every 5K, bus service to the start and a finisher medal.
The 11th Annual F.O.R 5k Trail Race takes runners through the scenic McDonald Nature Preserve in Wilbraham. This family-friendly trail run supports the local parks' maintenance fund.
Run or walk through the scenic orchards of New Paltz at this chip timed 5k event featuring homemade donuts and fresh cider for all finishers.
A student run community event on April 25, 2026 at MacDuffie School in Granby, MA featuring a flat cross country 5K and an optional Color Run, with 100% of proceeds going to Dakin Humane Society.
Experience a technical 5 mile trail run through 250 acres of scenic green space in Killingworth. Navigate rocky terrain and elevation shifts at the Deer Lake Outdoor Center with awards for multiple age categories.
A 12 mile out and back trail race on the Holyoke Ridge near Amherst MA featuring technical singletrack, over 3,500 feet of ascent, a 500 runner cap and a waitlist when full.
A technical out and back 50K on New Haven blue trails with about 6,350 feet of climbing, strict time cutoffs, no crews or pacers, and multiple aid stations including water only stops.