Massachusetts
Massachusetts Trail Running Calendar 2026-2027
Explore the best trail runs in Massachusetts for 2026-2027! Our updated list features 61 exciting trail runs across the region. Find your next trail run in Massachusetts below and join the trail community at these great events!
August 2026
An inclusive trail festival at Northfield Mountain offering a 20k prediction run, an untimed 5k fun run/hike (about 6k), a kid's run, and a virtual option.
A timed, summit-driven trail event on Wachusett Mountain offering 7, 14, 21, and 28-mile options, optional weighted vests for bonus swag, and up to 10 hours to complete the marked course.
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.
A trail 5K at Felix Neck Wildlife Sanctuary in Edgartown on September 5, 2026, with a 0.25 mile kids run for ages eight and under. Registration has set fees and bib pickup is handled at the sanctuary and proceeds support conservation.
Charity 5K run and 1.5 mile walk in Huntington MA on a mixed pavement, field and trail course that finishes at Littleville Dam.
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 1 mile inflatable fun run and walk at Butterfield Park in Orange, MA raising funds for Fisher Hill School sixth grade trip fundraising, with advance registration at $15.
Cross country meet in Franklin Park with 5 km and 8 km races on September 19, 2026; entry fee $15 and minimum age 16.
A non-competitive women only 5K obstacle mud run at Carter & Stevens Farm in Barre, MA on September 20, 2026, featuring 18 plus obstacles and a teamwork focus.
Backyard Ultra in Leominster State Forest on September 26, 2026; runners repeat a 4.167 mile loop each hour until only one remains.
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
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.
Lake Wallace Fall Fest on October 3, 2026 in Belchertown offers a 5K, a 1K accessible run, a Roll & Stroll, vendors, live music, and fundraising for trail accessibility.
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.
Join the annual Run Stanley event at Stanley Park for a variety of trail races including a 5K K9 run and an accessible 1 mile stroll. Support local wildlife sanctuary maintenance while enjoying a community day in the park.
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.