Trail Running calendar near Westport 2026-2027

A beach fun run at Sandy Neck Beach in Barnstable with 3K and 5K sand courses where participants walk, run, or crawl. Proceeds support MSOA scholarships for marine biology students and a partner scholarship effort in 2026.

A 3 mile trail run through Sakonnet Vineyard in Little Compton followed by dinner, wine and music among the vines. Race entry includes timing, a t shirt and a souvenir wine glass; dinner only options are also available.

Experience a point to point trail race in Northeast Connecticut on the Airline Trail. Choose between marathon, half marathon, and 10K distances with individual or relay team options to support local student education.

A six hour weighted lap race on Mansfield's WWII Veterans Memorial Trail where competitors carry chosen weight each lap and earn Kz by multiplying measured weight by lap distance; the highest Kz in each division wins.

United We Move Trailfest on October 17, 2026 at Fall River Bioreserve offers walk, run, and ride routes of varying lengths to support the Annual Campaign; routes are marked and GPX files are available.

Trail races in Wompatuck State Park near Hingham MA featuring a one loop 10 mile and a three loop 50K. Aid stations supply water and snacks and proceeds support Friends of Wompatuck, Free to Run, and Footprints.

A fall trail event at Grills Preserve in Westerly with 10 mile and 10 km courses across single-track trails and riverfront sections. Club timing is used, orange clothing is required, and post-race refreshments are provided.

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 fall trail 5k in Berkley MA combining running, rucking, and walking to honor military, first responders, and K9s. Dogs are allowed on leash with a waiver and proceeds support local canine and service organizations.

A fall trail race at Powisset Farm in Dover on October 25 2026 offering four distances, one water aid station, post race cider donuts and family activities with awards for top finishers.

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 two day obstacle event at Fenway Park in Boston featuring a Stadion 5K with 20 obstacles, a kids race, and spectator access. The course uses stadium features including the Green Monster, clubhouse, and home plate.

A November trail festival at Willowdale State Forest in Ipswich offering multiple looped distances from a 10K to 100K, a Cider Donut Mile, and a flagged 0.5‑mile youth run, with cupless aid stations and fundraising for local land trusts.

A looped trail event at White Barn Farm in Wrentham, MA on Nov 7, 2026, featuring 3.1 mile laps on grass and dirt. Distances range from 5K to 50K so participants can choose how many laps to run.

A 5k chip-timed run/walk at Stonington Vineyards on November 8, 2026 featuring a two-lap cross country route through the vines. Registration includes a shirt, collapsible wine glass, finisher medal and a pour of wine.

Trail races in Upton State Forest include a 10.5K loop and a 13.1 mile half marathon run as two laps. Aid stations are spaced about every 3 miles and post race offerings include fire pits, hot soup and hot chocolate.

Push your limits on the scenic wooded trails of Wright Locke Farm with the TARCkey Trot, a 6 hour timed event run on a repeated 5K loop. Bring your own cup and register online early as day of registration is not offered.

A November trail race at Burlingame State Park offering 4 mile and 8 mile courses on dirt trails and roads, a required orange garment mandate, post-race food, and age group awards for both distances.

A trail running event at Middlesex Fells Reservation with **8 mile**, **32 mile**, and **40 mile** loop options on the white blazed Skyline Trail. The course is technical and minimally marked, cupless with two aid stations and specific cour..

Celebrate the twentieth anniversary of this unique cross country race held at the Mount Hood Golf Club. Choose between a competitive three and a half mile run or a festive two mile walk through hilly terrain.