Ipswich
Trail Running Calendar near Ipswich 2026-2027
Explore the top trail runs near Ipswich for 2026-2027! We've gathered 20 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Trail Animals Running Club stages a multi-distance trail event at Great Brook Farm State Park, from a free 0.5 mile youth run up to 50 miles, on marked looped courses.
Cross-country races at Great Brook Farm State Park in Carlisle MA on 09/13/2026, featuring a 2K youth race and multiple 5K fields as part of the USATF New England Grand Prix.
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.
A 5K on October 24, 2026 at Stratham Hill Park that runs along Great Bay and benefits Great Bay Stewards; the mostly downhill course includes a race shirt for timely registrants and a bib with a beer or cider coupon.
November 2026
Two-day Spartan Stadion weekend at Fenway Park in Boston featuring a Stadion 5 km with 20 obstacles plus kids races around 1 to 1.5 km.
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.
A community 5K through campus trails with a free kids fun run, raffle, awards, and a 200 participant limit.
A community trail event at Good Pickin’ Farm with a scenic 5 mile run, a 2.5 mile walk or run, and a 1K kids run plus post race farm activities.
A community memorial run in Tyngsboro, MA with a 1.5-mile walk and two 5K options, raising funds for a school scholar/athlete award and science scholarships while maintaining a tradition of food donations.
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.