Trail Running calendar near Greenwood 2026-2027

Experience an unapologetically wild mountain crossing in the White Mountains of New Hampshire. Navigate rugged, unmarked ridgelines across 25K, 25 mile, or 50 mile distances in this remote wilderness challenge.

Traverse five peaks across 26 miles of spectacular Vermont terrain in this mountain trail challenge. This community event offers multiple distance options and over 6,000 feet of elevation gain through the Northeast Kingdom.

Experience the natural beauty of Maine by running or walking through woodland trails in Arundel. This conservation focused event offers 5k, 10k, and half marathon distances along with a kids bike race and live music.

Experience a trail-only loop course through Wolfe's Neck Center and Freeport Conservation Trust. This cup-less event offers distances from 10 to 50 miles on a scenic route featuring dirt roads, woods, and local bridges.

Experience an annual half marathon on the tallest mountain in Southern Maine. Run across technical single track and mountain ridges to support local land conservation and trail maintenance.

Experience the ultimate test of endurance in Center Conway at this last person standing ultramarathon. Run a scenic 3.5 mile forest loop every hour until only one participant remains.

Experience the Bobcat Ridge 25K trail race at the Edwin L Smith Preserve in Maine. This event features a limited field of 100 runners and supports the Kennebunkport Conservation Trust.

The Mile for Mentoring will take place in Gilford on Sunday 4 October 2026.

The Devil's Den Ultra challenges runners on a rugged 6.4-mile Vermont trail loop. Choose from a 30-hour, 12-hour, or single-loop 10K race. Every finisher earns a unique Devil tarot card, with more cards awarded for major milestones in the t..

Teams compete on a 278 yard obstacle course featuring hurdles and a water hazard. This unique event in the Maine mountains rewards the winners with their partner's weight in beer and five times their weight in cash.

The Cranmore Mountain Race is a classic two lap mountain run in New Hampshire. Runners tackle ski slopes and trails for a share of $7500 in prizes. This historic event is part of the USATF New England Mountain Circuit.

Experience a timed mountain trek across the rugged ridges of Vermonts Northeast Kingdom. Choose from multiple loop distances and the option to carry weighted gear for an added challenge on the scenic trails of Burke Mountain.

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.