Redmond
Trail Running Calendar near Redmond 2026-2027
Explore the top trail runs near Redmond for 2026-2027! We've gathered 19 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A trail event near Sisters Oregon featuring a 50K to the edge of the Three Sisters Wilderness and a point to point half marathon with a net downhill. The race supports the Sisters Trail Alliance and includes a shuttle to the start.
October 2026
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.
Mountain trail races on Mount Bachelor over October 3–4, 2026, including 6/12/24-hour summit loops and three looped courses. Chairlift use is included and multiple aid stations and lodge facilities support runners on alpine singletrack.
A fall trail running weekend at Suttle Lake, Oregon featuring 24 hour, 12 hour and 6 hour timed races on a 3.6 mile loop, free on-site camping, provided food, and basic facilities with portable toilets.
November 2026
Run The Rock in Smith Rock State Park near Bend Oregon features scenic loop trail races of 50K, 25K and a half marathon with significant elevation gain, single track sections, and aid stations.
April 2027
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 Alliance.
A four-race Thursday evening trail series in Bend OR from April 22 to July 15 2027 with courses of 4 to 7 miles and overall series standings.
May 2027
Sisters Country offers spring trail racing in Sisters, Oregon with a 50K and a Half Marathon, both starting and finishing at Village Green Park on May 2, 2027. The event includes aid stations, finisher medals, post-race food, and a local high sch..
A women-focused running event in Bend offering a half marathon, 10K, 5K and a kids run, with aid stations, gear drop, post-race vendors, and a community beneficiary supporting outdoor access for youth of color.
Nighttime trail event at Cline Buttes near Redmond OR featuring a 3.1 mile loop with Last Person Standing and multiple timed races.
Trail races of 50 mile, 50K, and 10 mile around Smith Rock State Park featuring basalt cliffs, Crooked River Grasslands, and Cascade Range views.
July 2027
A multi-discipline endurance festival in Bend, Oregon combining a half-marathon trail run, mountain bike and gravel races plus solo and team competition.
Point-to-point trail races from Bend to Sisters, Oregon, offering 100 mile and 50 mile options with aid stations, shuttle service, and a Western States qualifier for the 100.