Hamilton
Trail Running Calendar near Hamilton 2026-2027
Explore the top trail runs near Hamilton for 2026-2027! We've gathered 32 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Run the winding single lane trails of Groton Town Forest with a choice of 9.5 mile or 3.4 mile courses featuring roots, rocks and rolling climbs. Limited to 250 runners, this community race supports Groton trail maintenance and finishes with snacks.
A harvest-season 5K trail event at White Barn Farm in Wrentham with off-road terrain, a midway water station, bib pick-up the day before, family Harvestween activities, and a portion of registrations donated to the local food pantry.
A backyard ultramarathon at Waters Farm with a one loop hourly race, a 4.2 mile community run, a free kids fun run, and a full festival day.
A fall trail event in Harvard on October 25, 2026 featuring a 5K through orchard and woods plus a 1 mile kids fun run, with age divisions, awards, shirts, and proceeds benefiting the Harvard Conservation Trust.
A community fundraiser on October 25, 2026 featuring a timed 5K trail, a 1K pre-teen road race, a 5K walk, children's games and a costume contest.
Trail races at Assabet River National Wildlife Refuge in Sudbury MA with 10K, 30K and a 6-hour timed loop event on dirt and gravel double-track trails.
A continuous 50-mile trail race on a 3.1-mile loop in Wrentham, MA, with chip timing, a 12-hour cutoff, and a 75-runner field limit.
November 2026
A farm festival in North Grafton on November 1 with a 5K and kids run, apple tastings, hayrides, vendors, music, and activities supporting local hunger relief.
Trail half marathon and 10.5K in Upton State Forest on November 8, with limited entries, aid stations, and post race amenities.
A family friendly run and walk at West Thompson Dam on November 8, 2026 featuring a timed 5K trail run, a 3K untimed walk and a free kids 1/4 mile run; proceeds support local trails, parks and a food pantry.
Trail races of 5.3 miles and 10 miles through Callahan State Park with road sections to and from Brophy Elementary in Framingham.
A multi terrain 5K, a scenic 2 mile walk and a kids loop at Old Sturbridge Village on November 15, 2026 with awards and participant shirts.
A scenic 5K trail run in Wrentham, MA on November 26, 2026 with awards, post-race donuts and cider, a raffle, and a $25 registration fee.