Trail Running calendar near Redmond 2026-2027

The 34th Annual OXFORD Classic in Bend adds a Community 5K at Drake Park on 10/03/2026. The flat loop follows the Deschutes River on grass and paved paths and registration is free.

Alpine trail races on Mount Bachelor on October 3–4, 2026, featuring timed summit loops and three loop distances with chairlift access, on-mountain aid stations, parking and camping near West Village Lodge.

Trail races in Rainbow, Oregon offering a 20K and a 50K with more than 8,000 feet of climbing, old growth forest, and summit views. Shuttle service, multiple aid stations, and food at the finish are provided.

Timed loop events at Suttle Lake in Sisters, OR offer 24 hour, 12 hour and 6 hour formats on a 3.6 mile loop with 110 ft gain per loop. Free camping and one main aid station are available.

A Halloween themed ranch run in Sisters, Oregon featuring a chip timed 5k run, 5k walk, 5 mile race, and a free kids dash. Included swag, a costume contest, live music, and post race non alcoholic beverages and snacks.

Run The Rock is a trail race weekend at Smith Rock State Park near Terrebonne, Oregon offering 50K, 25K and half marathon loop courses. Courses feature substantial climbing, single-track trails and staffed aid stations.

Trail race on Cline Butte near Redmond, Oregon offering a 20 Mile summit route with about 2000 ft gain and a scenic 15K with about 400 ft gain, featuring runnable sections, technical rocky trail, and wide mountain views.

A trail running event near Sisters, OR on April 11, 2027 offering 40 mile, trail marathon and 20 mile courses on Peterson Ridge and Metolius Windigo trails. The Rumble raises funds for Sisters High School Cross Country and Sisters Trails Al..

A spring trail event in Sisters, Oregon featuring a 50K and a Half Marathon that start and finish at Village Green Park. The 50K includes 2400 ft of climbing and five aid stations; the half has 700 ft of climbing and two aid stations.

A 230 mile point-to-point endurance run across the Oregon Outback, held July 16–21, 2027. The route crosses remote volcanic and basin landscapes, travels on lands important to regional tribes, and includes a 120 hour cutoff and pacer rules.