Trail Running calendar near Leyden 2026-2027

A 12 mile out and back trail race on the Holyoke Range in Amherst, MA with more than 3,500 ft of elevation gain on technical singletrack. Runners must carry their own water and two manned stations are provided.

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..

Trail event in Pittsfield, Vermont, May 6 to 9, 2026, offering distances from 10 miles to 200 miles through the Green Mountain National Forest. Team entries can secure the same start time and service member discounts are available.

Multi distance trail races along the Wapack Trail from Mount Watatic to North Pack Mountain. The technical, rocky course has large elevation gain, five aid stations, drop bag service and limited entries.

Trail race on Winant Park Trails in Concord, NH offering approximately 3.9 mile and 7.0 mile routes. Proceeds support the Ralph Waldo Emerson School for Preschoolers and day of entry is available.

Spring Fling 600 in Southington, CT on May 9, 2026 features a 600 minute looped trail event and a 6 Mile race at YMCA Camp Sloper. Both events use chip timing and offer finisher medals and awards for top competitors.

A community 5 km run and walk on May 9, 2026 at Pinkerton Academy in Derry, NH, with a course across campus and nearby cross-country trails. Proceeds support the Pinkerton Fund to benefit students.

A 5K trail run in Hanover New Hampshire held on Mother’s Day, featuring packed trails, open fields and mellow single track. Pre registration is online only and race day registration is available with different fees by age group.

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 event on rugged Ragged Mountain in Berlin CT where runners repeat a roughly 3.11 mile loop each hour until one runner remains. Entry is limited to 55 and proceeds support local trail and youth running programs.

A dirt road 50k in Leyden, Massachusetts on May 16, 2026, with 4,200 feet of elevation change and a course that passes through forests, fields, and an 1870s covered bridge. Registration closes May 13 and there is no race-day entry.

A 5 km cross-country event at Canterbury Shaker Village on May 16, 2026 with in-person and virtual options. Online registration closes May 15 at 12:00 noon ET and the registration fee is $25.

A May race day on the Ashuwillticook Rail Trail offering a marathon, half, 8K and kids mile, with race shirts, finisher medals, aid stations, and proceeds supporting trail maintenance.

Trail running in Pittsfield State Park with 50K, 25K and a 5 mile course on single track and flowy forest trails. The event is organized by BURCS and benefits local animal rescue organizations.

A 50-mile point to point ultramarathon from Manchester to Mount Monadnock with about 6000 feet of gain over roads, dirt roads and trails. The course is GPX only with minimal markings, five aid stations, and a 125-runner cap.

Run or walk a 5k on the Southern New England Trunkline Trail in Franklin. This event supports the development of an abandoned rail bed into a multi use path connecting local communities.

Wason Pond Wrangler is an obstacle race on May 16, 2026 in Chester, New Hampshire, featuring a 5 km course run in multiple waves including a competitive wave. Online registration is closed and the event is limited to 800 participants.

A chip timed 5k at Ledge Rock Hill Winery in Lake George, NY, on a cross country style out and back course. Race swag includes a T shirt, a shatterproof collapsible wine glass and a medal, with age group awards and charity partner Nik's Wis..