Trail Running calendar near Windham 2026-2027

We have found 76 Trailruns within 80 miles of Windham. See below where and when you can find the races.

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.

October 2026

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.

November 2026

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.