Trail Running calendar near Windham 2026-2027

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 a scenic downhill course along the shores of Great Bay or take on the virtual 55K challenge. Support local estuary conservation while enjoying a community race that includes a long sleeve shirt and a post race beverage.

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.

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.

A rugged trail event at Pawtuckaway State Park near Nottingham, NH, offering a half marathon and a 5 mile course across boulder fields, single track, streams and the rocky Devil's Staircase. Three aid stations and time cutoffs are in place.

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.

A looped trail event at East Windham Conservation Area with a 50k run made of five 6.5 mile loops and a single loop 10k. Aid stations, lap-based results, and volunteer tracking support runners on a course with about 900 feet of climb per lo..

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.

Experience a classic New England trail event at Willowdale State Forest featuring multiple distances from 10K to 100K. Run through rolling terrain on a course celebrated for its community spirit and long history.