Massachusetts
Massachusetts Trail Running Calendar 2026-2027
Explore the best trail runs in Massachusetts for 2026-2027! Our updated list features 40 exciting trail runs across the region. Find your next trail run in Massachusetts below and join the trail community at these great events!
October 2026
A continuous 50-mile trail race on a 3.1-mile loop in Wrentham, MA, with chip timing, a 12-hour cutoff, and a 75-runner field limit.
A 5K on October 31, 2026 at AD Makepeace in Wareham MA around cranberry bogs, with on-site registration, age-group awards and a connection to the Cranberry Educational Foundation.
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.
Thanksgiving Day 5K cross-country run/walk at Maudslay State Park supporting local charities, organized by Joppa Flats and Winners Circle Running clubs.
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.