Trail Running calendar near Warren 2026-2027

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 trail event at Camp Greenough offering a 5K loop, a 10K two-loop option, and a six hour endurance challenge. Participants may run or ruck with specified weight standards and complete as many closed-course loops as they choose.

A backyard ultramarathon and festival at Waters Farm in Sutton MA where runners complete a 4.167 mile loop each hour on the bell until one remains. The weekend features live music, hay rides, a kids fun run, farm tours, and local food.

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.

Trail races through Powisset Farm and Noanet Woodlands in Dover MA with 8.6, 5.6, 3.1 and 1.5 mile options, post-race cider donuts and family activities.

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 stadium stair-climb at Gillette Stadium where participants run, walk, or roll through about 5,184 steps in support of Homes For Our Troops. The event offers team and wheelchair waves, optional fundraising, and spectator registration.

Obstacle course weekend at Fenway Park with a Stadion 5 km featuring 20 obstacles, kids races and spectator access on November 7 and 8, 2026.

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 last runner standing backyard ultra on private farmland in Winchendon with a 4.1666 mile loop. The event also offers 6 hour, 12 hour and 24 hour timed options plus a standalone fastest lap competition.

A looped 3.1-mile trail course at White Barn Farm in Wrentham MA with distances from 5K to 50K and a central aid station. Runners complete repeatable laps and may stop after any finished loop.

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 offer 10.5K and half marathon options over technical, hilly single track and forest roads. The event has a 250 runner cap and aid stations spaced roughly every three miles.

A family friendly run and walk at West Thompson Dam on November 8, 2026 featuring a timed 5K trail run, a 3K untimed walk and a free kids 1/4 mile run; proceeds support local trails, parks and a food pantry.

A 6 hour timed trail race on a 5K loop at Wright Locke Farm in Winchester Massachusetts, featuring rocky rolling singletrack, a barn aid station in a cupless format, and provisions for adaptive athletes and youth discounts.

A community 5K walk and run with a kids fun run at Windham Woods School on November 14, 2026 in Windham, NH.

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.