Trail Running calendar near Hillsborough 2026-2027

A 4.9 mile mountain trail race in Keene, NH featuring four up and down laps on varied ski and single-track trails, with proceeds and food donations benefiting the Keene Community Kitchen.

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.

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, timed 5K trail run at Wells Reserve at Laudholm on October 31, 2026 that raises funds for 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.

Timed 6, 12, 24 and 30 hour loop events on the New Boston Rail Trail with a 4.0 mile marked loop, central aid station, and awards for 100 mile finishes.

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.

Night-time trail races of 5k and 10k at Cranmore Resort on November 7, 2026, requiring headlamps and featuring reflective course markers and LED lighting.

Looped trail event at White Barn Farm on Nov 7, 2026, where runners complete 3.1 mile loops and choose how far to go.

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.

5K walk and run on Windham Woods School trails with a kids fun run, raffle, guaranteed shirts for registrations by October 15, and a 200 participant limit.

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 Last Person Standing mountain event with hourly 2.25 mile laps that climb about 1,209 feet each. Aid, hot food, camping, elevation milestone prizes, and awards are provided; conditions may include cold, snow, or ice.

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

Trail Animals Running Club hosts the TARC Winter Classic on December 5 in Middlesex Fells, offering 8, 32, and 40 mile looped trail races with marked Skyline Trail routes.