Trail Running calendar near Winchester 2026-2027

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.

Holistic Hustle in Kennebunkport features a timed 5K, a trail 10K and a kids half mile fun run at Emmons Preserve on October 31, 2026. The community fundraiser includes music, family activities, finishers medals and a raffle.

A costumed 5K trail run on October 31 2026 at Wells Reserve at Laudholm. Timed course with water stations and awards, with proceeds supporting coastal conservation and restoration.

Hugs From Vets Trail 10Kish in Henniker, New Hampshire on November 1 features a mixed trail and country road course and raises funds for American Legion Post 78. The field is limited to 150 participants and awards are given to overall and a..

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.

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.

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.

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.

A 4 mile trail race in Mine Falls Park with a post race party, raffle, awards, and proceeds supporting the Nashua Children's 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.