Massachusetts
Massachusetts Trail Running Calendar 2026-2027
Explore the best trail runs in Massachusetts for 2026-2027! Our updated list features 65 exciting trail runs across the region. Find your next trail run in Massachusetts below and join the trail community at these great events!
November 2026
A backyard ultra weekend at Kenty’s Farm with a 4.16667 mile loop, Last Runner Standing format, and timed 6/12/24/48-hour events plus themed community hours.
Obstacle course weekend at Fenway Park in Boston on Nov 7 and 8 2026 featuring a 5 km Stadion with 20 obstacles and kids races.
A November trail festival at Willowdale State Forest offering races from 10K to 100K, a cider donut mile, and a free youth fun run.
Trail event at Wompatuck State Park with a single 4 mile loop, an open 8 hour multi loop format, and a non eliminative Backyard style option.
Trail half marathon and 10.5K in Upton State Forest on November 8, with limited entries, aid stations, and post race amenities.
A hilly 5K at Pine Banks Park in Melrose supporting Melrose High School cross country teams, with overall and age group awards and post race refreshments.
Six-hour timed trail race on a 5K loop at Wright Locke Farm in Winchester MA with rocky rollers, a cupless barn aid station, and a youth discount.
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 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 Thanksgiving 5 km at Maudslay State Park on Nov 26 that merges WCRC Run For Pie with the Newburyport Turkey Trot, donating 100% of profits to local food charities.
An annual 5 km run and walk in Hopedale, MA that raises funds for local fire and police equipment and community programs.
December 2026
TARC Winter Classic at Middlesex Fells offers 8 mile, 32 mile and 40 mile loop races on technical, white blazed Skyline Trail with cupless aid stations and enforced cutoffs.
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.
March 2027
Trail races and a 1 mile Color Run in Salisbury on March 27, 2027, featuring 10K, 5K and a non timed color run, with proceeds supporting Salisbury Parks and Recreation.
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 running at Wompatuck State Park in Hingham MA with a four mile loop offered as a single loop, an eight hour accumulation, or a relaxed Backyard style option.
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.
Trail event in Hadley MA on April 25, 2027 with a 5K and a one mile Mushroom Mile, on-campus trails, a virtual 5K option, and proceeds to The Hartsbrook School.