Gloucester
Trail Running Calendar near Gloucester 2026-2027
Explore the top trail runs near Gloucester for 2026-2027! We've gathered 13 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.
October 18 trail race in Gloucester, MA through Ravenswood Park on single track and carriage roads, 4.1 miles; online registration closes Oct 15 and race day registration is available.
November 2026
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.
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.
A chip timed 5K trail race and kids fun run at Odiorne Point State Park supporting Marine Mammal Rescue, with race shirts, age group prizes, and a post race beach cleanup.
June 2027
A 20 mile single-loop hike through Wompatuck State Park on June 5, 2027, with aid stations, a finisher medal and on site parking.