Trail Running calendar near Portland 2026-2027

Discover the beauty of Emmons Preserve at a community event featuring trail races and family activities. Enjoy music and local treats while supporting holistic education through a variety of distances for runners and walkers.

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.

Nighttime mountain races at Cranmore Resort on November 7, 2026 featuring 5 km and 10 km courses, reflective markers, required headlamps, and post-event pizza and awards.

A Thanksgiving morning trail event in Jackson NH featuring a 5k on the Jackson nordic trails and a 1k kids fun run for age ten and under, staged at Eagle Mountain House with proceeds supporting local youth programs.