Trail Running calendar near Redmond 2025-2026

Mastondon is a 10ish mile early season trail run near Bend, Oregon on March 1 2026, rolling through juniper and high desert with mountain views. Expect a relatively flat course, one aid station, and post race food and beer.

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 the FootZone Dirty Half, a 13.1 mile trail half marathon through Bend Oregon's scenic National Forest trails on June 6, 2026. Expect dirt roads, sweeping forest views, a finisher prize and awards plus raffle prizes for top finishers.

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..

Run the shaded trails around Timothy Lake at the Mt. Hood Trail Runs July 11 and 12, 2026, with 25K, 50K and 50 mile options on scenic, occasionally technical forest routes along the Pacific Crest Trail. Limited fields; registration opens J..

On July 11 in Bend, Oregon, Bend Dirt Fest is a multi discipline endurance festival with trail, mountain bike and gravel distances for solo riders or teams. Enjoy scenic courses, local aid stations and a lively race day atmosphere.

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.

Join the 10th annual Hoodoo Challenge Run To The Top on Saturday July 25, 2026 at Hoodoo for a scenic climb to Potato Hill. Pick a half marathon or a 5K to the summit, then enjoy a hosted lunch and the awards ceremony.

Trail runners will love Haulin' Aspen in Bend Oregon, with a full marathon, half marathon and a 6.5 miles course through Deschutes Forest. Runners start and finish at Wanoga Sno Park at 5,500 feet amid pine forest and challenging climbs.

Challenge yourself on volcanic alpine trails at Mt. Bachelor, climbing to a 9,000 foot summit across loop distances and a straight up 5K ascent. Expect rugged terrain, full course support, and epic summit views near Bend, Oregon.

Run the Three Sisters Skyline in Sisters, Oregon with 50K and half marathon options that finish in town. Experience Ponderosa pines, alpine meadows and streams while supporting Sisters Trail Alliance and earning a finisher medal.

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 Community 5k at the 34th Annual Oxford Classic in Bend Oregon, a free, open to all loop through scenic Drake Park along the Deschutes River. Flat, wide paths make it ideal for a relaxed jog or lively pack racing.

Run The Rock invites trail runners to tackle scenic single track around iconic Smith Rock and high Cascade peaks near Bend, Oregon. Choose a 50K for big climbs and views or a half marathon for a spirited taste of the same terrain.