Westford
Trail Running Calendar near Westford 2026-2027
Explore the top trail runs near Westford for 2026-2027! We've gathered 38 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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
Two-day Spartan Stadion weekend at Fenway Park in Boston featuring a Stadion 5 km with 20 obstacles plus kids races around 1 to 1.5 km.
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 6 hour timed trail race on a rocky 5K loop at Wright Locke Farm in Winchester MA with a single barn aid station and a cupless format.
A community 5K through campus trails with a free kids fun run, raffle, awards, and a 200 participant limit.
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 through Callahan State Park finishing at Brophy Elementary School in Framingham, with mile markers and commemorative gifts.
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.
A 4 mile trail race in Mine Falls Park with a post race party, raffle, awards, and proceeds supporting the Nashua Children's Home.
December 2026
Celebrate the twentieth anniversary of this unique cross country race held at the Mount Hood Golf Club. Choose between a competitive three and a half mile run or a festive two mile walk through hilly terrain.
February 2027
Winter trail event at Hale Education in Westwood, MA offering 15 mile and 30 hour looped courses with marked trails, cupless aid stations, and strict cold-weather gear rules.
April 2027
10 mile trail race on April 10, 2027 in Andover MA along the Merrimack River with aid stations, handmade prizes, and proceeds supporting trail maintenance.
Trail Animals Running Club stages a looped trail event at Jericho Town Forest with 10K, half marathon, marathon and 50K options, marked course and a single cupless aid station.
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.