Orange
Trail Running Calendar near Orange 2026-2027
Explore the top trail runs near Orange for 2026-2027! We've gathered 14 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
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
A community fall event at Lake Wallace in Belchertown with a 5K, an accessible 1K, a Roll & Stroll, vendors, live music, and donations to the Lake Wallace Gift Account.
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.
Inaugural trail event in Dublin NH with a 5K and a 1 mile kids fun run on October 10, 2026 supporting the Dublin Consolidated School PTO.
A fundraiser featuring a 5K trail run and a half mile Little Leaf Dash through the Winston Prouty campus forest and fields with family activities.
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 5-mile mountain trail race at Granite Gorge with four laps and about 1650 feet of elevation, held to benefit the Keene Community Kitchen.
November 2026
A backyard ultra style last runner standing event in Winchendon MA on a 4.1667 mile loop with multiple timed formats and a fastest lap option.
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
Obstacle course weekend at Carter & Stevens Farm in Barre MA with Sprint, Super, and kids races plus spectator access on June 26 to 27, 2027.