Trail Running calendar near Drake Crossing 2026-2027

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 mile mountain trail race on Mt. Hood with a crew accessible lollipop loop, 17,300 feet of ascent and descent, staged at Mt. Hood Meadows.

11th annual trail race at Left Coast Estate on August 1, 2026, featuring 5K and 10K courses through oak savanna and vineyards, with proceeds funding oak savanna restoration.

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.

A weekend of timed running in Salem with 24 hour, 12 hour, and 6 hour events on a 1.05 mile loop, with a staffed aid station and chipped timing.

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.

Mountain trail races at Mt. Hood Meadows on August 15-16 2026, featuring a 50K USATF Trail National Championship, multiple distances and a free kids race.

A trail half marathon in Hood River, Oregon on August 22, 2026 with about 2,300 ft of elevation gain, mountain views and creek crossings. The event is cupless, requires personal water, includes two official aid stations and finisher prize b..

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 cross country 5k on a flower farm in Tillamook, Oregon, featuring mud pits, two river crossings, wood-chipped trails, a corn maze, and fields of flowers. Two open races are held with combined results.

The Long Watch is a 6 hour, 12 hour and 24 hour loop endurance event at Donald Farm in Woodland, Washington, held alongside the Warrior Expo, with a manned aid station and a one mile loop past competition and vendor areas.

Point to point 50K on the Pacific Crest Trail from the South Washington Cascades to the Columbia River Gorge with a detour to Three Corner Rock.

A multi-distance run in Portland offering a 50K and an about 53 mile route, mostly flat with a short technical Forest Park trail and no aid stations.

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 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.