Oxford
Trail Running Calendar near Oxford 2026-2027
Explore the top trail runs near Oxford 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.
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 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 technical single-track, significant climbs, one aid station, post-race food and beer, and proceeds supporting land conservation.
October 2026
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.
The 26th North American Wife Carrying Championship returns to Sunday River in Newry, Maine on October 10, 2026. Teams of one man and one woman race a 278 yards obstacle course with log hurdles, a sand trap, and the Widow Maker water hazard.
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.
July 2027
A 5K obstacle course at Sunday River Resort in Newry, Maine, featuring ski-trail and wooded terrain with custom built obstacles.