Windham
Trail Running Calendar near Windham 2026-2027
Explore the top trail runs near Windham for 2026-2027! We've gathered 22 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
The event is cancelled. It had been planned as a 10K ruck obstacle course at Pineland Farms in New Gloucester, Maine, featuring The Crucible with 20+ obstacles and prize rules requiring participants to ruck the full course with a pack.
A 4.5 miles trail race on Frye Island on 08/08/2026 that starts and finishes at the Community Center and loops around the island through wooded trails. Registration opens 07/10/2026 and the fee is $10.
A rugged 12 mile single track loop at Bradbury Mountain State Park, part of a small series and capped at 160 runners.
Third annual PRHS XC Alumni Race in Minot, Maine on August 22, 2026 features a 5K, a kids fun run, a barbecue and a kickball game.
A community race day at Cumberland Fairgrounds with a farmer’s market and music. Events include mile races, a kids 200 meter gallop and an open 5k that finishes on the horse track.
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 free Kids 1K at Skyline Farm through fields, hills and woods with prizes, food and music.
Trail races of 5k, 10k and half marathon on the Arundel Community Trails with medals, shirts, live music and a kids bike race.
A 21k trail race on Pleasant Mountain in Bridgton, ME, featuring steep ridge climbs, technical single-track, one aid station, and a finish-area afterparty with food and beer.
October 2026
A 25K trail race at Edwin L. Smith Preserve in Kennebunkport, ME on October 3, 2026, with proceeds benefiting the Kennebunkport Conservation Trust and registration capped at 100.
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.