Winchendon
Trail Running Calendar near Winchendon 2026-2027
Explore the top trail runs near Winchendon for 2026-2027! We've gathered 20 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
An inclusive trail festival at Northfield Mountain offering a 20k prediction run, an untimed 5k fun run/hike (about 6k), a kid's run, and a virtual option.
A timed, summit-driven trail event on Wachusett Mountain offering 7, 14, 21, and 28-mile options, optional weighted vests for bonus swag, and up to 10 hours to complete the marked course.
September 2026
Pisgah Mountain Trail Races in Chesterfield, NH offers 50k and 23k mountain trail ultraruns on Sunday 9/13/26. Aid stations provide LMNT, Tailwinds, and Untapped and proceeds support New Hampshire Special Olympics.
A 1 mile inflatable fun run and walk at Butterfield Park in Orange, MA raising funds for Fisher Hill School sixth grade trip fundraising, with advance registration at $15.
A community 5K in Jaffrey, NH offering a woods trail and a rail trail out and back. Proceeds support the volunteer Jaffrey Firefighters Company and equipment needs of the Jaffrey Fire Department.
An 18 mile out and back trail race from Windblown Ski Area in New Ipswich NH to Watatic Mountain in Ashburnham MA with steep technical terrain and a three hour turnaround cutoff.
A non-competitive women only 5K obstacle mud run at Carter & Stevens Farm in Barre, MA on September 20, 2026, featuring 18 plus obstacles and a teamwork focus.
Backyard Ultra in Leominster State Forest on September 26, 2026; runners repeat a 4.167 mile loop each hour until only one remains.
October 2026
Experience the peak of New England autumn on a journey through the mountains and fields of central Massachusetts. This trail event offers three distances crossing state borders for runners seeking adventure on the Midstate Trail.
A time-based event in New Salem MA offering 12 hour and 24 hour run or walk options around the town common on October 11, 2026.
A multi format trail event on the Granite Town Rail Trail in Brookline and Milford NH on October 17 and 18 2026, featuring 7.5 mile relays, 15 mile and 30 mile races and a 30 hour ultramarathon. Proceeds support local trail conservation.
A 5-mile mountain trail race at Granite Gorge with four laps and about 1650 feet of elevation, held to benefit the Keene Community Kitchen.
A fall trail event in Harvard on October 25, 2026 featuring a 5K through orchard and woods plus a 1 mile kids fun run, with age divisions, awards, shirts, and proceeds benefiting the Harvard Conservation Trust.
November 2026
Timed loop event in New Boston NH offering 6, 12, 24 and 30 hour individual and relay options with chipped bib tracking and a central aid station.
A backyard ultra at Kenty's Farm in Winchendon MA on Nov 7 2026 featuring a 4.16667 mile loop plus 6, 12 and 24 hour timed options.
May 2027
Trail ultramarathons on the Wapack Trail in Ashburnham, MA with 21.5, 43, and 50 mile options over rocky, technical terrain and significant elevation gain.
June 2027
An obstacle race weekend at Carter & Stevens Farm in Barre MA featuring a Sprint 5K with 20 obstacles, a Super 10K with 25 obstacles, and kids races.