Portland
Trail Running Calendar near Portland 2026-2027
Explore the top trail runs near Portland for 2026-2027! We've gathered 12 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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 community run at Emmons Preserve in Kennebunkport featuring 5K, 10K trail and a kids fun run with medals, music, family activities and a raffle.
A costumed 5K trail run at Wells Reserve at Laudholm on October 31, 2026, supporting coastal conservation with timing, water stations, T-shirts, and awards.
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.