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Trail Running Calendar near Quincy 2026-2027

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Explore the top trail runs near Quincy for 2026-2027! We've gathered 33 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's fall trail race in Carlisle features looped courses from 10K to 50 miles, a youth fun run, marked aid stations, and a cupless policy.
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.
Cross country meet in Franklin Park with 5 km and 8 km races on September 19, 2026; entry fee $15 and minimum age 16.
Trail races and a 6 hour timed event through Assabet River National Wildlife Refuge with aid stations, cupless rules, pacer options, and proceeds supporting refuge projects.
October 2026
Timed trail event in Cumberland RI on a 4.2 mile loop offering 8 hour, 12 hour and 34 hour solo and team formats with distance awards and a large pit area.
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 5K run and fitness walk at Highland Park in Attleboro on October 4 2026. The traffic free grass course uses two laps of a 1.55 mile loop and includes a kids 100 yard dash plus a virtual 5K option.
Trail races at Houghton's Pond in the DCR Blue Hills Reservation follow rolling dirt roads and forest paths with rocks and roots. Two distances are offered, about 7 miles and 3.7 miles, with notable elevation change on each course.
On October 11, 2026 the HFC Striders Cross Country Festival returns to Wayland for its 20th running, featuring 3K youth races across age groups and two 5K open races, with awards and proceeds benefiting Wayland High School.
Six hour weighted trail race on Mansfield's WWII Veterans Memorial Trail where competitors carry chosen weight over repeated laps to score pound miles (Kz).
A community 5K through Lincoln MA roads, fields and trails on October 18 2026 with proceeds benefiting the Lincoln Land Conservation Trust.
Trail event at Wompatuck State Park on October 24, 2026 offering a one-loop 10 mile and a three-loop 50K with three aid stations and a nine hour cutoff.
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 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.
A rugged 5k trail event in Berkley, MA offering running, rucking, walking, and separate kids and dog entries, with fundraising and support for K-9s and first responders.
Trail races through Powisset Farm and Noanet Woodlands in Dover MA with 8.6, 5.6, 3.1 and 1.5 mile options, post-race cider donuts and family activities.
A stadium stair-climb at Gillette Stadium raising funds for Homes For Our Troops, covering about 5,184 steps in the lower bowl with individual, team, and fundraising options.
November 2026
Obstacle course weekend at Fenway Park featuring a Stadion 5 km with 20 obstacles, kids races of 1 to 1.5 km, and spectator access.
Looped 3.1 mile trail at White Barn Farm with a stocked aid station and cumulative distances from 5K to 50K.
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