Trail Running calendar near Windsor 2026-2027

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.

Rock The Ridge is a fundraising trail event at Mohonk Preserve on May 2, 2026. Options include a 50 mile ultra, a 26.2 mile trail marathon and relay teams, with proceeds supporting conservation and education.

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 four race 5 km trail series at Cole's Woods in Glens Falls across Tuesdays in May, with a 20 km challenge for those who complete all four events. Entry fees, T shirt allocation, awards and proceeds benefiting the Glens Falls Youth Center..

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.

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 community event on May 9, 2026 featuring a Family Color Run and a 5K Trail Run at Hamden and New Haven YMCA locations. Registration runs from Feb 20 to May 8 with entry fees of $10 and $30; first 100 pre-registrants receive a Y giveaway.

A 5K trail run through the orchard at Indian Ladder Farms on May 10, 2026, with a hard cider mimosa provided after the finish and non alcoholic options; top 1st to 3rd place finishers aged 21 and over receive craft cider bottles.

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.

Tails & Trails State Forest Run in Pittsfield State Park on May 16, 2026 features 50K, 25K and a 5 mile loop of single track, pine forests and mountain bike style trails while supporting local animal rescues.

Event Overview The Ledge Rock Hill Wine Run 5K takes place at the Ledge Rock Hill Winery in Lake George, New York. The event features a 5K distance, which is open to participants aged 1 to 99. It is a timed race, with professional timing an..

Trail races at Soapstone Mountain in Stafford Springs, CT include a new half marathon and the Jerry Stage 6K Sampler. Courses run on the blue blazed Shenipsit Trail through Shenipsit Forest with on course aid for the half marathon.

Run a 3.5-mile trail race in Wolcott, CT. The event supports the local cross country teams. Your entry includes access to the CT Food Truck Battles Festival afterward.

A one-day return of the Somers Summer 5K on May 17, 2026 at Field Road Park; entry is free and registration runs from August 28, 2025 to May 16, 2026. Proceeds support improvements to the park fitness trail.