Oregon
Oregon Trail Running Calendar 2026-2027
Explore the best trail runs in Oregon for 2026-2027! Our updated list features 87 exciting trail runs across the region. Find your next trail run in Oregon below and join the trail community at these great events!
September 2027
A checkpoint run in Mt. Tabor where participants receive a map and choose their own routes to collect as many checkpoints as possible within a two hour limit.
Trail races at Tollgate, OR on the Umatilla Rim including a new 23 miler plus half, 11K and 7K, all on single track with marked aid stations and finishers' swag.
October 2027
A community 5K within the long-running Oxford Classic, this flat mixed-surface loop in Drake Park follows the Deschutes River and is open to all ages.
A last person standing trail race on Hamilton Island with repeated 4.13 mile loops; runners start each hour and continue until one remains.
A two day October trail event on the Upper Rogue River featuring point to point 50 Miler and 50K races plus looped Half and 12K runs.
Fall trail races in Tillamook Forest featuring a steep, technical 25K summiting Elk and Kings mountains and an 11 mile point to point on the Wilson River Trail.
A weekend of trail races Oct 3-4, 2026 in Yachats and Cape Perpetua with 50K, 20 mile, half marathon and 10K courses along coast and forest.