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.
September 2026
Trail Fest in Arundel offers 5k, 10k and half marathon courses on the ACT and Eastern Trails, with medals, shirts, a kids bike race, live music and food.
A 21k mountain race in Bridgton featuring technical single track trails and significant elevation gain across the iconic ridge of Pleasant Mountain.
A 5K held at Bowdoin College on September 27 2026 featuring a two-lap grass and dirt trail course around the Pickard Field complex with a $20 entry fee.
October 2026
A 25K trail race at Edwin L. Smith Preserve in Kennebunkport, Maine on October 3, 2026, with proceeds supporting the Kennebunkport Conservation Trust.
A 5k trail run and walk in Oxford, Maine, starting and ending at Oxbow Beer Garden to benefit Mission Working Dogs, offered in-person and virtually.
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
July 2027
Back Cove Backyard Ultra in Portland ME features roughly 4.16 mile hourly loops on the Back Cove Trail repeated until one runner remains.
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.