Princeton
Trail Running Calendar near Princeton 2026-2027
Explore the top trail runs near Princeton for 2026-2027! We've gathered 26 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
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.
Trail races in Upton State Forest offer 10.5K and half marathon options over technical, hilly single track and forest roads. The event has a 250 runner cap and aid stations spaced roughly every three miles.
A community trail event at Good Pickin’ Farm with a scenic 5 mile run, a 2.5 mile walk or run, and a 1K kids run plus post race farm activities.
Trail races of 5.3 miles and 10 miles in Callahan State Park with indoor facilities, course markings, water stops, and age group log trophies in Framingham, MA.
A community memorial run in Tyngsboro, MA with a 1.5-mile walk and two 5K options, raising funds for a school scholar/athlete award and science scholarships while maintaining a tradition of food donations.
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.