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Trail Running Calendar near Weston 2026-2027

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Explore the top trail runs near Weston for 2026-2027! We've gathered 43 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.
Veterans Count Nashua 5K in Nashua, NH on September 5, 2026 is a community 5K with free T shirts for registrations by July 20 and free kids entries.
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.
A trail-based 5K run/walk and a 3K walking route at Mine Falls Park supporting Meals on Wheels of Hillsborough County, with a $30 registration and a 2026 event T-shirt for early registrants.
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.
Run for Nature on September 27, 2026 at Shedd Park in Lowell offers 5K, 10K and a 1 mile kids run to support local conservation and education.
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 trail race and 5K walk through Lake Street Park trails, plus a Kid Run on the lacrosse field for age 12 and under.
Trail races in Groton Town Forest on October 4, 2026 offering 9.5 mile and 3.4 mile courses with limited fields and online registration.
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.
Backyard ultramarathon at Waters Farm with a 4.167 mile hourly loop, a 4.2 mile community run, a free kids fun run, and a full festival.
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