Trail Running calendar near Wrentham 2026-2027

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 4.9 mile mountain trail race in Keene, NH on October 25, featuring four up and down laps on different trails, 1650 feet of elevation, prize money and age group awards, with proceeds supporting the Keene Community Kitchen.

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 run at Powisset Farm in Dover, MA with four distances on meadow and woodland trails, a cupless aid station, post race cider donuts and family activities including a barnyard and pumpkin painting.

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.

A 10K trail race in Penwood State Park featuring technical single track on the Metacomet Trail and rocky runnable terrain. No aid stations so runners must carry hydration for 6.2 miles; proceeds partly support NAMI.

A stadium obstacle race weekend at Fenway Park on November 7-8, 2026 featuring a 5 km Stadion with 20 obstacles, a kids race, and spectator access inside and around the historic ballpark.

The Hamsterwheel in New Boston, NH features timed 6, 12, 24 and 30 hour events on a scenic 4.0 mile loop along the New Boston Rail Trail, with chip timing, a central aid station, team entries, and buckle awards for 100 miles.

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.

Windham Woods School holds its 3rd annual Thankful Trails 5K on November 14, 2026 with a two loop 3.1 mile trail course, a free Kids Fun Run for ages 8 and under, an event raffle, and a limited field of 200 participants.

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 community memorial run in Tyngsboro, MA with a 1.5-mile walk and two 5K options, raising funds for a school scholar/athlete award and science scholarships while maintaining a tradition of food donations.