Portland
Trail Running Calendar near Portland 2026-2027
Explore the top trail runs near Portland for 2026-2027! We've gathered 16 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
Timed mile races, a kids 200 meter gallop and an open 5k at the Cumberland Fairgrounds on 08/30/2026 with prize payouts and nonprofit beneficiaries.
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 walk at Skyline Farm across fields, rolling hills and woods, with a free kids 1K, after-race food, music and prizes.
A trail festival in Arundel offering 5K, 10K, a half marathon and a free kids' bike race on scenic ACT and Eastern Trail routes.
October 2026
A 25K trail race at Edwin L Smith Preserve in Kennebunkport on October 3, 2026, with proceeds supporting 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.
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.
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.
A short, non-competitive 2.5 mile trail run at Thorne Head Preserve with river views, a fall breakfast, finisher mugs, and proceeds supporting local trails and education.
A costumed, timed 5K trail run at Wells Reserve at Laudholm on October 31, 2026 that raises funds for coastal conservation and restoration.
July 2027
Back Cove Backyard Ultra in Portland ME has runners repeat an about 4.16 mile loop each hour on the scenic Back Cove Trail until only one runner remains.