Gloucester
Trail Running Calendar near Gloucester 2026-2027
Explore the top trail runs near Gloucester for 2026-2027! We've gathered 11 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
An annual 5K cross country run or walk in Franklin Park supporting Boston Latin School Athletics. Team registration is new for 2026 and fees are tiered with free entry for BLS students.
A 4.1 miles trail race in Ravenswood Park, Gloucester, held October 18, 2026, as part of the North Shore Trail Series. The course uses single-track and carriage roads, with online registration closing October 15 and race-day registration available.
November 2026
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 rocky 5K loop at Wright Locke Farm in Winchester MA with a single barn aid station and a cupless format.
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.
March 2027
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.
Annual fundraising run at Odiorne Point State Park featuring a chip timed 5K, kids runs, race shirts, prizes, and a post event beach cleanup.
June 2027
MammothMarch Boston is a 20 mile hiking event on June 5, 2027 at Wompatuck State Park with aid stations, on-site parking, a finisher medal, and certificates.