Bridgton
Trail Running Calendar near Bridgton 2026-2027
Explore the top trail runs near Bridgton for 2026-2027! We've gathered 18 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 21k trail race on Pleasant Mountain in Bridgton, ME featuring steep ridge climbs, technical single track, one aid station, and an afterparty with food, beer 21+, and live music.
October 2026
A last person standing trail ultra in Center Conway NH on October 3, 2026 run on a 3.5 mile forest loop with a minimal aid station, camping option, and a Sunday Beer Mile.
A 5 km trail run and walk starting and ending at Oxbow Beer Garden in Oxford, ME on October 4, 2026, benefiting Mission Working Dogs with a course on Anne's Moon Dance.
A 100k trail run and bike event in Norway, Maine on October 11, 2026 combining 25k running and 75k cycling across six trail systems to benefit local nonprofits.
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.
November 2026
Trail 5 km Turkey Trot in Jackson, NH with a 1 km kids fun run, awards for top finishers, and proceeds benefiting local youth programs.