Gloucester
Trail Running Calendar near Gloucester 2026-2027
Explore the top trail runs near Gloucester for 2026-2027! We've gathered 14 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
November 2026
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 in Hingham offering a single 4 mile loop, an eight hour loopathon, and a Backyard style hourly format with a lenient non elimination rule.
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.
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.
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
Ten mile trail race along the Merrimack River in Andover with USATF sanction, post race refreshments, awards, and proceeds supporting local trail maintenance.
May 2027
June 2027
A 20-mile single-loop hike at Wompatuck State Park on June 5, 2027, with aid stations, finisher medal, certificate and about 950 ft of elevation gain.