Trail Running calendar near Chester 2026-2027

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.

Join this dog friendly 5K trail run at Blydenburgh County Park to support animal rescue. Enjoy a scenic multi surface course with refreshments and professional timing included for all participants.

Test your endurance on a scenic five kilometer trail loop in Wrentham Massachusetts. This supported race offers forty and fifty mile challenges with a twelve hour cutoff and consistent access to aid stations.

Experience a community trail event in Cross River featuring a competitive 5k race, a scenic 4k walk, and a 200m kids dash. Explore the wooded hills of the John Jay Community Trail ending at the campus contest field.

Experience a unique all terrain run through Heckscher Farm and wooded trails in Stamford. Runners pass farm animals and historic landmarks on a scenic course while children enjoy a dedicated fun run and educational activities.

Experience a beautiful trail run through the Irvington Woods with 5K and 1K distances. This rain or shine community event features finishers medals for all participants and supports the Irvington Bulldog Booster Club.

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.

A point-to-point trail race on the Long Island Greenbelt Trail with 50K and 25K options, fully stocked aid stations, parking at Heckscher Park, and a two-hour trail-volunteer requirement for entrants.

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.

The final Conquer the Trail Race is a 7.5 km run on the flat Croton Aqueduct Trail. This special edition supports Mercy University's Mav Market and celebrates the school's 75th anniversary. The event offers awards, raffles, and free parking..

The Brookhaven Trail 15K and 4 Mile runs explore the varied paths of Brookhaven State Park. This cupless event is capped at 250 runners and includes awards, refreshments, and supports veterans and local food banks.

A five-week open-course trail running series in Poughkeepsie, NY, presented by Fleet Feet Poughkeepsie and powered by HOKA. Limited to 65 participants; registration runs March 18 to April 20, 2026 with a $60 fee.

A women only trail running event at Lake Mohegan in Fairfield, Connecticut on April 25, 2026, organized by Steep Endurance to raise awareness of trail running for women. Entry fees are listed between $30 and $80.

Experience three seasons of trail running and walking through scenic conservation land and a working vegetable farm in Wrentham with this unique 5K triple series.

Experience a scenic 5k trail run through conservation land and working farmland in Wrentham. Celebrate Earth Day with an off road course featuring natural obstacles and community focused agriculture support.

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 the Leatherman's Loop 10k trail race at Ward Pound Ridge Reservation in New York. Entry is managed via a lottery system for this USATF sanctioned spring event through the local woods.

Try the Trail is a youth trail run for ages 4 to 16 at Katonah Memorial Park. Kids can choose between a half-mile or one-mile course on scenic, easy-to-follow trails. It's a family-friendly event focused on outdoor activity.

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.