Trail Running calendar near Westwood 2026-2027

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 late-October trail race at Mt. Tom State Park with solo and two person relay options on rugged single-track courses, multiple distances, regular aid stations, significant elevation, and proceeds supporting land conservation.

A trail race in Keene, New Hampshire covering 4.9 miles with about 1650 feet of up and down on ski trails and single track. The event benefits the Keene Community Kitchen and includes prize money, age group awards, and raffles.

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 Stadion 5K obstacle race at Fenway Park on Nov 07 - 08, 2026 with 20 obstacles, a kids race, and spectator access; the course uses the clubhouse, Green Monster area, and finishes at home plate.

Timed multi-hour trail event on a marked 4.0 mile loop near the Hillsborough County Fairground in New Boston, NH. Multiple solo and relay options from 6 to 30 hours, chip-timed with a central aid station and specific pacer and crew rules.

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 backyard ultra at Kenty’s Farm in Winchendon MA on November 7, 2026 where runners repeat 4.1666 mile laps until one remains. The event also offers 6, 12 and 24 hour timed options plus a single lap competition.

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 Thanksgiving themed timed 5k run and walk at Stonington Vineyards on November 8, 2026 featuring vineyard scenery, chip timing by J3 Timing, event shirts, a collapsible wine glass, a wine glass shaped finisher medal and a pour of wine.

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.

Enjoy a festive four mile trail race through the wide paths of Mine Falls Park. All proceeds from the run and raffle support residential and educational programs at the Nashua Childrens Home.

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.