Windham
Trail Running Calendar near Windham 2026-2027
Explore the top trail runs near Windham for 2026-2027! We've gathered 14 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Trail 5k in Oxford, Maine with in person and virtual options, starting and ending at Oxbow Beer Garden to benefit Mission Working Dogs.
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.
Community fundraising hike at Lost Valley where participants repeat climbs over a four hour challenge to raise funds for Tree Street Youth.
A community run at Emmons Preserve in Kennebunkport featuring 5K, 10K trail and a kids fun run with medals, music, family activities and a raffle.
November 2026
June 2027
A 6 mile trail race in Pownal, ME, part of the Bradbury Mountain series; capped at 140 runners with a 1 hour 48 minute cutoff.
July 2027
Back Cove Backyard Ultra in Portland, ME on July 10, 2027 has runners complete a roughly 4.16 mile loop each hour until only one runner remains, with staffed aid and free parking.
A 9 mile two lap trail race on Bradbury Mountain with hilly technical single track, capped at 140 runners and organized by nonprofit Trail Monster Running.
August 2027
A twisting 12 mile single track trail race at Bradbury in Pownal, ME, capped at 140 runners and closing the Bradbury Mountain Trail Race Series.
September 2027
Backyard ultra race on a 4.2 mile wooded loop in New Gloucester, Maine, with double track, moderate elevation gain, and a $150 registration fee.