Trail Running calendar near Westwood 2026-2027

Experience New Hampshire’s original 30 hour ultramarathon on the historic Granite Town Rail Trail. Choose from multiple distances and relay options in this flat and fast Halloween themed fundraiser for local trail conservation.

A six hour weighted lap race on Mansfield's WWII Veterans Memorial Trail. Competitors carry measured weight each lap and score pound-miles called Kz, with the highest total in each division winning.

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.

Join a community trail race through the diverse terrain of Wompatuck State Park. Choose between a ten mile loop or a 50K distance on a course featuring rail trails and single track paths.

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 race at Mt. Tom State Park on October 24, 2026, with single and relay options from 5k to 25k on rugged single-track terrain. The event supports Kestrel Land Trust and includes aid stations, medical crews, and awards.

A 5K on October 24, 2026 at Stratham Hill Park that runs along Great Bay and benefits Great Bay Stewards; the mostly downhill course includes a race shirt for timely registrants and a bib with a beer or cider coupon.

A timed trail event at Camp Greenough on a fully closed 5K loop offering Run or Ruck divisions across 5K, 10K, and a 6-Hour endurance challenge, with set ruck weight standards and separate rankings by division.

A mountain trail race in Keene NH on October 25, 2026 covering 4.9 miles with 1,650 feet of elevation across four laps; the event benefits the Keene Community Kitchen and offers 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 stair climb at Gillette Stadium where participants walk, jog or climb around the lower bowl while music and team highlights play. Net proceeds support Homes for Our Troops.

A Stadion 5K obstacle race at Fenway Park on November 7-8, 2026, featuring 20 obstacles and a finish across home plate. The weekend also includes a 1 to 1.5 km kids race, spectator tickets, team options, and a service member discount.

A multi hour loop event on the New Boston Rail Trail near the fairgrounds offering 6, 12, 24 and 30 hour individual and relay options, chip timing, a central aid station, team entries, pacer rules and 100-mile buckles.

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 on November 7, 2026 where runners complete repeated 4.1666 mile laps until one remains; also offers 6, 12 and 24 hour timed options and a single-lap competition.

Looped trail event at White Barn Farm featuring a clearly marked 3.1 mile loop and a fully stocked aid station. Participants stack laps to reach distances from 5K up to 50K, with each completed loop recorded.

A Thanksgiving themed chip timed 5k at Stonington Vineyards on November 8, 2026. The event features vineyard scenery and includes a t shirt, a portable wine glass, a finisher medal that doubles as a wine stopper and a wine pour.