Trail Running calendar near Chesterfield 2026-2027

A 123-mile point-to-point ultramarathon across Connecticut with a 36-hour limit, a mix of trails and roads, multiple mid-course cutoffs, and solo and relay options; finishers receive a buckle, medal, and event t-shirt.

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.

Trail loop event at Penwood State Park with 17K and 50K options on rocky single track and forest roads. The 50K uses three loops on much of the Metacomet Trail and carries a nine hour cutoff.

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 trail race at Jericho Town Forest (Weston, MA) on April 25, 2026 offering 10K, half, marathon, and 50K options on a marked 10K loop, cupless aid station, strict cutoffs, and parking by volunteers.

A spring trail race at Grafton Lakes State Park covering about 9.3 miles with roughly 900 feet of elevation gain. Trails are technical yet runnable and the course can be muddy in spring.

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.

The A Run to Remember will take place in Red Hook on Saturday 2 May 2026. You can run between 5 and 10 kilometers.

Experience the beauty of the Shawangunk Mountains with a 50 mile ultra, a trail marathon, or a team relay. Enjoy well maintained carriage roads and an 18 hour cutoff in this premier fundraising event for Mohonk Preserve.

Celebrate National Truffle Day with a chocolate themed trail run at Giddings Park. This event features a three loop 5K for all ages and a kids fun run to support Franklin Elementary School programs.

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.

Experience a trail run or walk through the campus of The Hartsbrook School in Hadley. Choose between a 5k or a 1 mile race on natural terrain while supporting local land stewardship and agricultural education programs.

Trail races in Lyme, Connecticut offering a 9.2 mile loop and a 3 mile sprint on Mount Archer trails. Chip timed and rain or shine, with 100% of proceeds donated to local emergency services.