Portland
Trail Running Calendar near Portland 2026-2027
Explore the top trail runs near Portland for 2026-2027! We've gathered 13 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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 the Wells Reserve at Laudholm on October 31, 2026 supporting coastal research, with timed results, water stations, awards, and a limited shirt.
November 2026
ACT Trail Fest in Arundel, Maine features 5K, 10K and half marathon trail races, a free kids bike race, live music, food and shuttled parking.
February 2027
A 5 Miler running event in Pownal, Maine on February 7, 2027, organized by Trail Monster Running; registration opens November 1, 2026.
June 2027
A 6 mile trail race at Bradbury Mountain State Park in Pownal, ME, limited to 140 runners, with course rules, shirts, prizes, and series awards.
July 2027
Back Cove Backyard Ultra in Portland, ME has participants run an approximately 4.16 mile loop each hour on the Back Cove Trail until only one runner remains.
A 9 mile two lap trail race on Bradbury Mountain State Park featuring 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 Mountain State Park on August 8, 2027 with a 140 runner field cap and a 3 hour 36 minute cutoff.
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.