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.
August 2026
A 4 mile out and back beach run on Nantasket Beach in Hull, MA on August 6, 2026, held at low tide with a post-race gathering and proceeds supporting local causes.
A community trail run in Lynn, MA featuring a no-drop 5 km on gravel roads with refreshments and a shoe raffle at the Market Street Arc'Teryx storefront.
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
A November trail festival at Willowdale State Forest in Ipswich offering multiple looped distances from a 10K to 100K, a Cider Donut Mile, and a flagged 0.5‑mile youth run, with cupless aid stations and fundraising for local land trusts.
A 6 hour timed trail race on a 5K loop at Wright Locke Farm in Winchester Massachusetts, featuring rocky rolling singletrack, a barn aid station in a cupless format, and provisions for adaptive athletes and youth discounts.
December 2026
March 2027
April 2027
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
A 20 miles single loop hike through Wompatuck State Park near Boston on June 5, 2027 with aid stations, a finisher medal and a personalized certificate.