Hamilton
Trail Running Calendar near Hamilton 2026-2027
Explore the top trail runs near Hamilton for 2026-2027! We've gathered 24 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 community 5K in Quincy’s Merrymount Park with in-person and virtual options, raising funds for youth leadership, adult English classes, and mental health services for Asian and immigrant families.
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.
Trail event at Wompatuck State Park with a single 4 mile loop, an open 8 hour multi loop format, and a non eliminative Backyard style option.
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 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.
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