Massachusetts
Massachusetts Trail Running Calendar 2026-2027
Explore the best trail runs in Massachusetts for 2026-2027! Our updated list features 38 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
An annual festival at Brigham Hill Community Farm combining a community 5K and kids fun run with vendors, food, apple tastings, hayrides, and family activities.
Backyard ultra and timed 6, 12, 24 and 48 hour races near Winchendon MA on a 4.1667 mile mixed terrain loop with pompom hats for participants.
Two-day Spartan Stadion weekend at Fenway Park featuring a 5 km course with 20 obstacles, kids races, and spectator options.
November trail event at Willowdale State Forest offering looped distances from a free youth fun run to a 100K with fundraising for local land trusts.
Trail running at Wompatuck State Park with a 4 mile loop and three formats: a single loop, an 8 hour loop challenge, or a Backyard style option.
Trail races in Upton State Forest offering a 10.5K and a two-lap half marathon over technical, hilly single-track and forest roads with limited fields.
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.
A six hour timed trail race on a rocky 5K loop at Wright Locke Farm with a cupless aid station, goat companions, a $35 entry, and limited registration.
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.
DNRT’s 12th annual trail race on November 14 at Destruction Brook Woods offers a unique 5K and a 10 mile course with post-race pizza, beer, and recovery services.
Trail races of 5.3 miles and 10 miles through Callahan State Park with road sections to and from Brophy Elementary in Framingham.
A multi terrain 5K, a scenic 2 mile walk and a kids loop at Old Sturbridge Village on November 15, 2026 with awards and participant shirts.
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 trail 5K at Maudslay State Park merged with the Run For Pie event, with 100% of profits donated to local food charities and early shirt pick-up options.
An annual 5 km run and walk in Hopedale, MA that raises funds for local fire and police equipment and community programs.
A scenic 5K trail run in Wrentham, MA on November 26, 2026 with awards, post-race donuts and cider, a raffle, and a $25 registration fee.
A 5K and 1 mile Kids Fun Run at Patton Park on November 28, 2026, featuring age divisions, prizes, a Boston Marathon entry giveaway, and packet pick up options.
A family friendly 5k trail run and fun walk at Chesterfield Gorge with handmade hat prizes, cookie medals and a community potluck supporting Hilltown Land Trust.
December 2026
TARC Winter Classic offers 8, 32 and 40 mile looped races on the white blazed Skyline Trail in Middlesex Fells with technical terrain, minimal markings, and aid stations.
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.