Windham
Trail Running Calendar near Windham 2026-2027
Explore the top trail runs near Windham for 2026-2027! We've gathered 21 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
Timed mile races, a kids 200 meter gallop and an open 5k at the Cumberland Fairgrounds on 08/30/2026 with prize payouts and nonprofit beneficiaries.
September 2026
Test your endurance at Pineland Farms in Maine with this backyard ultra trail race. Run a 4.2 mile loop through pristine wooded trails and see how many laps you can complete in this last person standing format.
A trail running weekend around Mirror Lake in West Newfield, Maine, with laps of about 3.6 to 3.8 miles through forest roads and singletrack. The weekend includes a Saturday gravel ride, onsite camping, youth runs, and a post ride gathering with food..
A community 5K trail run and walk at Skyline Farm across fields, rolling hills and woods, with a free kids 1K, after-race food, music and prizes.
A trail festival in Arundel offering 5K, 10K, a half marathon and a free kids' bike race on scenic ACT and Eastern Trail routes.
A 21k trail race on Pleasant Mountain in Bridgton ME featuring technical single-track, significant climbs, one aid station, post-race food and beer, and proceeds supporting land conservation.
October 2026
A 25K trail race at Edwin L Smith Preserve in Kennebunkport on October 3, 2026, with proceeds supporting the Kennebunkport Conservation Trust and registration capped at 100.
A 5 km trail run and walk starting and ending at Oxbow Beer Garden in Oxford, ME on October 4, 2026, benefiting Mission Working Dogs with a course on Anne's Moon Dance.
A coastal 5K at Hermit Island Campground supporting Marine Mammals of Maine, with timed and untimed in-person runs, a weeklong virtual 5K, a kids 1-mile fun run, raffle, and prizes for top human and canine finishers.
A 32.5 mile five lap trail ultra in Windham, ME on Red, Blue and Purple trails with two aid stations per loop and volunteer support.
A fundraising community event at Lost Valley in Auburn where participants climb the access road repeatedly over four hours to raise money for Tree Street Youth.
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.
November 2026