Chelmsford
Trail Running Calendar near Chelmsford 2026-2027
Explore the top trail runs near Chelmsford for 2026-2027! We've gathered 35 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
Obstacle course weekend at Fenway Park featuring a Stadion 5 km with 20 obstacles, kids races of 1 to 1.5 km, and spectator access.
Trail festival at Willowdale State Forest with 10K, half, marathon, 50 mile, 100K, a Cider Donut Mile and a free youth fun run; proceeds support local land trusts.
A 6 hour timed trail race on a 5K loop at Wright Locke Farm in Winchester Massachusetts, featuring rocky rolling singletrack, a barn aid station in a cupless format, and provisions for adaptive athletes and youth discounts.
A community 5K through campus trails with a free kids fun run, raffle, awards, and a 200 participant limit.
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.
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
Experience a winter trail challenge at Hale Education featuring 15 mile and 30 hour options. Navigate three unique loops through the Massachusetts woods while testing your endurance and self reliance in cold weather conditions.
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
A trail running event on the Wapack Trail in Ashburnham Massachusetts with 21.5 mile, 43 mile, and 50 mile options across rocky, technical terrain with aid stations, drop bag support, and a manual timing system.