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
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.
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.
A fall festival in Tyngsboro featuring a 3K trail race, a free kids fun run for ages 7 and under, a farmer’s market, vendors, kids activities, and food on October 25.
November 2026
Obstacle course weekend at Fenway Park in Boston on Nov 7 and 8 2026 featuring a 5 km Stadion with 20 obstacles and kids races.
A November trail festival at Willowdale State Forest offering races from 10K to 100K, a cider donut mile, and a free youth fun run.
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.
A community 5K on the Windham Woods School campus with a two-loop trail course, a kids fun run, raffle, awards, and post-race lunch.
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.
A Thanksgiving 5 km at Maudslay State Park on Nov 26 that merges WCRC Run For Pie with the Newburyport Turkey Trot, donating 100% of profits to local food charities.
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.