Trail Running calendar near Sunriver 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..

Run the Incline Vista trail race in Redmond, OR and climb to Cline Butte for sweeping views of the Cascades, Smith Rock and the Ochocos. Choose a challenging 20 Mile or a runnable 15K across new connecting trails and varied singletrack.

Peterson Ridge Rumble near Sisters, Oregon offers 40 mile, trail marathon and 20 mile routes on scenic Peterson Ridge and Metolius Windigo. Limited to 500 runners, proceeds support Sisters High School cross country and Sisters Trails Allian..

Sisters Country on May 3 in Sisters OR hosts 50K and half marathon on scenic single track trails at Village Green Park. With manageable climbs, stocked aid stations and a burrito and beer finish, ideal for first time trail runners.

Smith Rock Classic at Skull Hollow near Terrebonne Oregon offers 10 mile, 50K and 50 Mile courses through Smith Rock and Crooked River Grasslands with basalt cliffs and Cascade views. Proceeds support Ridgeview High cross country.

Run laps on a flat 1.05 mile loop through scenic Elijah Bristow State Park, choosing 24 hour, 12 hour day, 12 hour night, or 6 hour time based challenges. Reach 100 miles to earn a buckle. Camping, crew space, and an aid station keep things..

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.

Oakridge Triple Summit Challenge in Oakridge OR, June 12 to 14, 2026, is a three day stage trail race with a combined 60k option and 28k, 17k, 15k plus a kids 1 mile. Rugged single track, summit views and post run food and drinks.

Experience waterfalls, lava flows and old growth forest on the scenic 31 mile McKenzie River Trail Run near Blue River, Oregon on June 13, 2026. Proceeds support McKenzie Bridge area non profits and aid stations keep runners fueled.

Alpine Solstice on June 20, 2026 at Swampy Lakes Sno Park near Bend Oregon offers scenic trail running through the Deschutes National Forest. Choose a new 55K past Tumalo Falls with Cascade peak views or a half marathon along Cascade Lakes..

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.

Tackle the Oregon Cascades 100, a point to point trail run from Bend to Sisters with 100 and 50 mile options through scenic single track and rugged terrain. The 100 mile is a Western States qualifier and awards a finisher buckle.

Haulin' Aspen near Bend Oregon offers marathon, half, or 6.5 mile Half As on scenic single track through Deschutes National Forest with big climbs and fast descents. Post race music, vendors and a beer support Bethlehem Inn.

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.

Run through Ponderosa pines, alpine meadows and mountain streams in Three Sisters Skyline, a scenic trail race near Sisters, Oregon with 50K and half marathon options. Both courses finish in town and benefit the Sisters Trail Alliance.

Mountain Lakes 100 is a scenic 100 mile trail race at Olallie Lake Resort, running between Mt Jefferson and Mt Hood with long stretches on the Pacific Crest Trail. Expect technical single track, big mountain views and a 150 person field.

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.

Run The Rock invites trail runners to Smith Rock State Park near Bend, Oregon, November 7 and 8, 2026 with a challenging 50K and scenic half marathon. Enjoy rugged single track trails, canyon views, and stocked aid stations.