Trail Running calendar near Maupin 2026-2027

Run the Three Sisters Skyline in Sisters, Oregon with 50K and half marathon options that finish in town. Experience Ponderosa pines, alpine meadows and streams while supporting Sisters Trail Alliance and earning a finisher medal.

Mountain Lakes 100 is a rugged 100 mile trail ultramarathon at Olallie Lake, Oregon, with about 60 miles on the Pacific Crest Trail and stunning mountain lake views. Technical terrain and well stocked aid stations reward determined runners.

Join the new Community 5k at the 34th Annual Oxford Classic in Bend Oregon, a free, open to all loop through scenic Drake Park along the Deschutes River. Flat, wide paths make it ideal for a relaxed jog or lively pack racing.

The Bachelor Summit Trailfest will take place in Bend from Saturday 3 October 2026 to Sunday 4 October 2026. You can run between 5 and 10 miles.

Run through lush forests and waterfalls at the 16th annual Silver Falls trail races in Silverton Oregon on Saturday October 17 2026. Choose from a 50K, marathon or 7 miler with limited entries opening August 1 2026.

Thunder River in Cascade Locks Oregon offers 50K and 25K trail courses on the Pacific Crest Trail, passing under the Bridge of the Gods and finishing at Marine Park. Expect scenic singletrack and dramatic Gorge views.

Run The Rock at Smith Rock State Park near Bend, Oregon offers scenic single track trail loops and big views. Pick a 50K or half marathon, earn a custom finish award, and support the Ridgeview High School cross country team.

The Ruff is a 7 mile out and back trail to Dog Mountain in the Columbia River Gorge, climbing about 3,000 feet on scenic single track before a fast descent. Finishers enjoy beer, pizza and podium awards.