Trail Running Calendar Oregon 2026-2027

Run through private vineyards near Dundee Billick Park with chip-timed races, a post-race festival featuring tasting from 25 wineries, and distances from a 5K to a half marathon plus a short wine walk and a virtual option.

Experience a 6 mile trail run through the Mt. Hood National Forest featuring stream crossings and steep terrain. Enjoy group camping and a post race beer garden at the McCubbins Gulch Campground.

A low-key evening trail running series in Forest Park, organized as three Series of five races with courses around 4 to 7 miles. The Series includes standings, a post-Series awards gathering, and benefits the Forest Park Conservancy.

A four-race trail series in Bend, Oregon held on Thursday evenings with courses from 4 to 7 miles across April to July 2026. Series registration covers all four races and single-race sign up is available on site for 25 USD cash.

A point to point trail event from Bend to Sisters with 100 mile and 50 mile options across Cascade single-track and mixed roads, staffed aid stations, and a Western States qualifier for the 100 mile distance.

Trail half marathon and 5K at Hoodoo on July 25, 2026. Scenic forest trails, summit views, limited fields, hosted lunch and awards.

Outlast Portland is a 6 hour trail challenge of six timed 5K laps run on the hour. Runners who complete four or five laps earn patches and those who finish all six earn a medal and a national leaderboard ranking.

A trail run near Oakridge, Oregon offering two single-track distances: a 14 mile course with 3300 feet of climb and descent, and a 5.5 mile point-to-point with shuttle service. Part of the Run Big Trail Series.

A low-key evening trail running series in Forest Park, organized as three Series of five races with courses around 4 to 7 miles. The Series includes standings, a post-Series awards gathering, and benefits the Forest Park Conservancy.

A 100 kilometre loop trail race near Oakridge, Oregon, starting at Willamette Pass Ski Area. The course climbs multiple peaks on mostly single track trails and features views of Waldo Lake; prior ultra experience is recommended.

A 100 mile mountain trail race around Mt. Hood with 17,300 feet of ascent and descent, staged at Mt. Hood Meadows. The crew accessible lollipop loop course features aid stations, chip timing and a finisher metal belt buckle.

A trail event at Left Coast Estate on August 1, 2026, with 10K and 5K run options and a 5K walk. Proceeds support the Oak Savanna Restoration Project and the day includes wine tasting, live music, and awards.

A remote mountain ultramarathon in the Elkhorn Mountains near Sumpter, Oregon, offering **53 mile** and **50K** courses. Prior trail ultramarathon experience is required; registration includes shuttle, post-race meal, finisher award, and fa..

Haulin Aspen is an all-trail running event on August 8, 2026 near Bend, Oregon. It features a full marathon, half marathon, a 6.5 mile course, and a new three person marathon relay on forested single track.

An 80.6-mile, six-person relay near La Grande, OR, featuring river-side highway sections, 20+ miles of gravel mountain roads, about 6,000 feet of elevation gain, and a finishing trail leg at the Anthony Lakes ski area.

Experience a 5k mud run and garden party at the Wooden Shoe Tulip Farm. This annual event combines an adventurous obstacle course with a vibrant flower festival to support local charitable community projects.

Angry Owl Ultramarathons in Salem, Oregon offers 24 hour, 12 hour and 6 hour timed runs on a 1.05 mile mixed surface loop with chip timing, a single aid station, and participant caps; 2026 marks the event's tenth year.

A two day Spartan Trifecta weekend on August 8-9, 2026 at Tom Pence Ranch, featuring Sprint 5 km, Super 10 km and Beast 21 km obstacle races plus kids races, workshops and a four hour Hurricane Heat event.

A 24 hour challenge at Elijah Bristow State Park where runners complete ten 5 km laps at 2.5 hour intervals. Camping, meals, drinks, event shirts and swag are provided and finishers receive a coffin style award.

A low-key evening trail running series in Forest Park, organized as three Series of five races with courses around 4 to 7 miles. The Series includes standings, a post-Series awards gathering, and benefits the Forest Park Conservancy.