Massachusetts
Massachusetts Trail Running Calendar 2026-2027
Explore the best trail runs in Massachusetts for 2026-2027! Our updated list features 60 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
A community fundraising day in Groton, MA on August 5, 2026 featuring an 8.4 mile three-person relay, kids single-loop race and Little Lambs mini runs, followed by barbecue and activities, with proceeds to six local charities.
A 4 mile out and back beach run on Nantasket Beach in Hull, MA on August 6, 2026, held at low tide with a post-race gathering and proceeds supporting local causes.
Trail Animals Running Club holds 10M, 50K and 40M trail races on a mostly forested 10-mile loop at Noon Hill Reservation in Medfield MA.
A community trail run in Lynn, MA featuring a no-drop 5 km on gravel roads with refreshments and a shoe raffle at the Market Street Arc'Teryx storefront.
A 5K off-road trail run, walk, and hike at White Barn Farm through Wrentham conservation land. The event is part of the Farm to Trail 5K Series and raises funds to support local agriculture and food pantry donations.
A chip-timed 5K run/walk at Brimfield Winery on a two-lap grass course with hills, race swag, a wine pour, and age group awards; a one-lap 1.5 mile division is available.
A timed six hour loop event on Aug 22, 2026 at Jug End State Reservation in Egremont MA with repeated 4.2 mile laps and a 0.75 mile final loop.
Trail runs over Vineyard Hill and through Bradley Palmer State Park offering 5K and 10K courses with one Start/Finish aid station, local prizes, and chip timing as part of the North Shore Trail Series.
A 5K cross country race at Waters Farm in Sutton Massachusetts that opens the USATF New England XC Grand Prix series. Separate men's and women's open races, on site registration, and a post race awards ceremony.
An inclusive trail festival at Northfield Mountain on August 29, 2026 that centers queer and trans runners and allies. It offers a 20k prediction race, an untimed 5k fun run or hike, and a Kid's Run with community-focused prizes.
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 hosts a multi distance trail event at Great Brook Farm State Park on September 5, 2026. Looped 10K and 10 mile courses cover distances from 10K to 50 miles, plus a youth fun run and a Yeti Mischief Mile.
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.
September 12, 2026 trail races in Pittsfield State Forest offering 50K, 25K, 15K and a new 5 mile option with proceeds supporting Free to Run.
Experience a fun inflatable obstacle course at Butterfield Park. This 1 mile run or walk supports 6th grade students at Fisher Hill School in reaching their educational trip goals through community participation.
GBTC XC Invite in Carlisle, MA features youth and Open/Masters cross-country races at Great Brook Farm State Park on September 13, 2026. Distances include a 2K youth race and multiple 5K races; registration runs August 1 to September 11.
A women only 5K obstacle mud run at Carter & Stevens Farm in Barre, MA on September 20, 2026. The course has 18+ obstacles, welcomes participants ages seven and up, and emphasizes teamwork over competition.