Chelmsford
Trail Running Calendar near Chelmsford 2026-2027
Explore the top trail runs near Chelmsford for 2026-2027! We've gathered 31 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
Trail races of 5.3 miles and 10 miles through Callahan State Park with road sections to and from Brophy Elementary in Framingham.
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.
Thanksgiving Day 5K cross-country run/walk at Maudslay State Park supporting local charities, organized by Joppa Flats and Winners Circle Running clubs.
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.
January 2027
Winter trail event at Hale Education in Westwood with a 30 hour ultra and a 15 mile looped course, marked trails, cupless aid stations, and required cold weather gear.
April 2027
USATF sanctioned 10 mile trail race in Andover MA with timed results, aid stations, baked prizes, and proceeds supporting Merrimack River Trail maintenance.
Trail Animals Running Club hosts looped trail races at Jericho Town Forest with 10K, half marathon, marathon and 50K options, a single aid station, and strict time cutoffs.
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.
August 2027
A timed, single-day endurance walk on Wachusett Mountain with 7, 14, 21, or 28 mile loops, optional weighted rucks, and aid stations about every 2.5 to 3 miles.