Trail Running calendar near Windsor 2026-2027

A 123 mile point to point ultramarathon across Connecticut featuring about 57 miles of trail, a 36 hour cutoff, solo and relay options, and belt buckles for 200K finishers.

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.

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 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.

A 12 mile technical out and back trail race on the Holyoke Range near Amherst, MA, with more than 3,500 ft of elevation gain. Rocky singletrack ridgelines, two manned water stations, and registration currently shows full with a waitlist.

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.

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.

A technical trail race on the Wapack Trail in Ashburnham, MA on May 9, 2026, offering 21.5, 43 and 50 mile options over rocky single track and significant elevation. Registration is limited, manually timed, and nonrefundable.

A dual-event day featuring a Family Color Run and a 5K Trail Run on May 9, 2026, in Hamden, CT. The first 100 to pre-register get a special giveaway, with water stations available for all participants.

Experience the eighth annual Spring Fling 600 trail races at YMCA Camp Sloper. Choose between a 6 mile race or a 10 hour challenge to complete as many loops as possible on a scenic three mile course.

A last person standing loop race on Ragged Mountain where runners repeat a roughly 3.11 mile loop and must finish each lap within one hour; entrants are eliminated if they fail to start or finish a lap, continuing until a single finisher re..

The Free Spirit 50K is a scenic ultra on the dirt roads of Leyden, Massachusetts. The route passes historic farms, forests, and a vintage covered bridge, offering a classic New England countryside experience.

Annual May races on the Ashuwillticook Rail Trail offering marathon, half and 8K distances starting and finishing at the Adams Visitors Center. Proceeds support the rail trail and a municipal fund for the City of Pittsfield.