Trail Running calendar near Redmond 2026-2027

Run roughly 10 miles through the high desert trails of the Maston network. This relatively flat course offers views of the Deschutes River and Central Oregon mountains. It's an early-season trail race on a scenic loop.

Incline Vista is a trail race on Cline Butte, offering stunning 360-degree views of the Cascades. Choose from a challenging 20-mile route with significant elevation or a scenic 15K course with varied terrain.

The Peterson Ridge Rumble is a trail running event in Sisters, Oregon, featuring three distances on scenic multi-use trails. It supports local youth running and trail advocacy. Finishers are celebrated with a post-race feast and unique sock..

Sisters Country offers a 50K and Half Marathon on the trails near Sisters, Oregon. Both courses start and finish at Village Green Park, featuring single-track paths and mountain views. It's a spring event supporting a local high school cros..

The Smith Rock Classic is a spring trail race through the iconic high desert landscape of Smith Rock State Park. Runners can choose from 50-mile, 50K, or 10-mile distances, each offering stunning views of the Cascade range. The event finish..

The Dirty Half is a 13.1 mile trail race in Bend, Oregon. The course starts on pavement before heading onto dirt and single-track trails through the National Forest. Every finisher gets a prize, and shirt sales support the Deschutes Land Tr..

Event Overview The Oakridge Triple Summit Challenge is a three-day stage trail running race held in Oakridge, Oregon. The event features multiple race distances taking place over three days, from June 12 to 14, 2026. Distances & Format..

The McKenzie River Trail Run is a 50K ultramarathon along a scenic trail featuring waterfalls and lava flows. It is Oregon's oldest continuous ultra, with registration including shuttle services and swag like a finisher's prize.

Celebrate the long days of early summer on the smooth singletrack trails near Bend, Oregon. Choose between a 55K course past Tumalo Falls or a Half Marathon. Enjoy a burrito and local beer after crossing the finish line.

The Mt. Hood Trail Runs offer 50M, 50K, and 25K distances on scenic trails near Oregon's highest mountain. With courses on the Pacific Crest Trail and around lakes, it's known for its volunteer support and community vibe. Finishers enjoy po..

The Bend Dirt Fest Half Marathon will take place in Bend on Saturday 11 July 2026. You can run 13 miles.

The Oregon Cascades 100 is a point-to-point trail ultra running from Bend to Sisters. Runners can choose between a 100 mile or 50 mile distance on a course featuring Cascade mountain trails. The event includes full aid stations, post-race m..

This trail running event features a half marathon and a 5K race. Both courses offer scenic forested paths and mountain views. The event includes a post race lunch and awards.

All-trail marathon, half marathon and a 6.5 miles course run on single track and forest roads near Wanoga Sno Park. Courses feature varied terrain, elevation change and multiple aid stations.

Challenge yourself on the volcanic alpine trails of Oregon’s Mt. Bachelor. Choose from four distances, all culminating in a summit finish at 9,000 feet. Experience rugged terrain and mountain hospitality with this Daybreak Racing event.

Run with stunning views of Oregon's Cascade peaks at the Three Sisters Skyline. Choose a scenic 50K on wilderness trails or a fast, net-downhill half marathon. Both races finish in the mountain town of Sisters.

Mountain Lakes 100 is a scenic 100-mile trail run starting at Olallie Lake, featuring 60 miles on the Pacific Crest Trail. All runners must complete a trail work requirement. It's a Western States qualifier with a field of 150.

Join the new Community 5k at the 34th Annual Oxford Classic in Bend. This flat and fast loop course runs through Drake Park along the Deschutes River. It's a chance to be part of a long standing regional cross country tradition.

The Bachelor Summit Trailfest offers alpine trail running adventures on Oregon's Mount Bachelor. Choose from timed loops or point-to-point races, with chairlift access between the start and finish villages. The high-elevation courses provid..

Run The Rock offers 50K, 25K, and half marathon trail races at Oregon's Smith Rock State Park in November 2026. Runners experience loop courses with views of the Cascade Mountains and unique rock formations. The event includes a military di..