Trail Running calendar near Willamette Pass 2025-2026

Kick off trail season at Mastondon on March 1, 2026, a scenic 10ish mile run near Bend and Redmond through juniper and high desert with views of the Deschutes River and surrounding peaks. Friendly early season course for adventurous trail r..

Incline Vista on Cline Butte near Redmond OR offers sweeping Cascade and Smith Rock views. Pick a summit focused 20 mile challenge or a scenic 15K with runnable stretches and rocky sections for a memorable trail day.

Run scenic ridge trails near Sisters, Oregon on April 12, 2026, choosing 20 mile, marathon, or 40 mile distances. Limited to 500 runners, the event benefits the Sisters High School cross country team and local trails.

Experience Sisters Oregon trails on May 3, 2026 with a rugged 50K or a flowing half marathon, both starting and finishing at Village Green Park. Enjoy stocked aid stations, pre race coffee and a post race burrito bar and beer while supporti..

Run Skull Hollow near Smith Rock with 50 mile, 50K and 10 mile courses on scenic single track and open grasslands. Finishers get awards, post race food and beer, and proceeds help a local high school cross country team.

Take on the Bristow Loop at Elijah Bristow State Park and see how many laps you can log on a flat 1.05 mile loop. Pick 6 hour, 12 hour day, 12 hour night, or 24 hour races and chase a 100 mile buckle.

Run the Dirty Half, a 13.1 mile trail through Bend Oregon's forests and single track, starting on pavement then winding into scenic National Forest trails. Finishers earn a prize and racers enjoy a lively community atmosphere.

Run 31 miles along the scenic McKenzie River corridor in Blue River Oregon, with aid stations, cupless service, and shuttle included. Proceeds support local nonprofits and entries are first come first served with a wait list.

Alpine Solstice on June 20, 2026 at Swampy Lakes Sno Park near Bend OR features a new 55K on mostly single track and a scenic half marathon through Deschutes National Forest. Enjoy post race food and beer while supporting Ridgeview team.

Bend Dirt Fest in Bend Oregon on July 11, 2026 blends trail running, gravel cycling, and mountain biking across scenic singletrack and gravel roads. Race solo or in teams and finish at the Athletic Club of Bend for lively festival vibes.

Take on the Oregon Cascades 100, a point to point trail race in Oregon offering 100 and 50 mile courses across mostly single track, big climbs, and scenic forest roads. A Western States qualifier with custom buckles for finishers.

Run scenic singletrack and forest roads from Wanoga Sno Park in Bend, Oregon with marathon, half marathon or a 6.5 mile option. Expect rolling terrain, steep climbs, fast descents and great mountain views.

Tackle volcanic alpine trails and climb to Mt. Bachelor summit near 9,000 feet at Bachelor Ascent, offering 50K, 28K, 16K and a Vertical Ascent 5K. Enjoy sweeping views, tough terrain and festival vibes in the West Village area.

Three Sisters Skyline in Sisters Oregon on September 19, 2026 offers a rugged 50K and a scenic half marathon that both finish in town. Run through Ponderosa pine forests, alpine meadows and along mountain streams for an unforgettable trail..

Join the new Oxford Classic Community 5k in Bend on Saturday, October 3, 2026, for a scenic loop at Drake Park along the Deschutes River. Flat, wide paths make it perfect for all abilities and family spectators.