Gloucester
Trail Running Calendar near Gloucester 2026-2027
Explore the top trail runs near Gloucester for 2026-2027! We've gathered 16 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
Community 5 mile trail run at Lynn Woods Reservation with a no drop pace, Norvan trail vest demos, post-run refreshments, and free parking.
Fall trail race in Ravenswood Park with single track and carriage roads, part of the North Shore Trail Series, offering onsite registration and postrace baked goods and raffles.
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.
A November trail event in Hingham MA offering a single 4 mile loop, an open 8 hour loop-count race, and a Backyard style hourly format that allows missed cutoffs.
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.
Thanksgiving Day 5K cross-country run/walk at Maudslay State Park supporting local charities, organized by Joppa Flats and Winners Circle Running clubs.
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
USATF sanctioned 10 mile trail race in Andover MA with timed results, aid stations, baked prizes, and proceeds supporting Merrimack River Trail maintenance.
May 2027
June 2027
A 20 mile single loop hike at Wompatuck State Park on June 5, 2027, featuring aid stations, a finisher medal, certificates, and varied trail terrain.