Trail Running Calendar Oregon 2026-2027

Join the 15th annual Ladybug Run at Cook Park for a scenic stroller friendly race along the Tualatin River. Support CDH awareness through various distances including a 5K, 10K, and kids events.

Run through scenic Oregon vineyards at Fueled by Fine Wine. Choose from a half marathon, quarter marathon, or 5k, followed by complimentary tasting from over twenty wineries. This event is limited to 1100 participants.

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..

Experience scenic forested trails and mountain views at the 10th anniversary of this trail running event. Choose between a half marathon to Potato Hill or a 5K race to the top of Hoodoo.

Test your endurance at this six hour trail challenge where runners must complete a 5K every hour to stay in the race. Finish all six rounds at Forest Park to earn your medal and a spot on the national leaderboard.

Experience 100 miles of diverse mountain terrain at the Hood Hundred on Mt. Hood. This Western States Qualifier features a scenic lollipop loop with 17,300 feet of ascent and professional event support.

Run for the Oaks is a 10th annual trail race through the vineyards and oak savannas of Oregon's Left Coast Estate. Proceeds support the Oak Savanna Restoration Project. The event includes wine tasting, live music, and a scenic course for ru..

The Elkhorn Crest 50 offers two rugged ultramarathon distances along Oregon's high mountain ridgeline. With courses averaging over 7,200 feet, runners experience technical terrain and panoramic valley views. This remote, advanced-level even..

Experience a pure trail running event in the Deschutes National Forest near Bend. Choose between a full marathon, half marathon, or the 6.5 mile course featuring beautiful mountain views and pine forest single track.

Gather your team of six for a scenic 81 mile relay through the mountains of Eastern Oregon. Experience 6000 feet of elevation gain across gravel roads and trails finishing at the beautiful Anthony Lakes.

Wy'East Trailfest offers a weekend of alpine trail running on Mt. Hood. Races range from a 50-mile national championship course to a family-friendly kids race. The event takes place at the Mt. Hood Meadows Ski Area.

Join the 12th annual trail half marathon in Hood River's scenic Post Canyon. This festive, inclusive event offers a challenging course with mountain views, waterfalls, and a supportive, party-like atmosphere. Every finisher gets a prize bag..

Experience the Oregon Coast with hilly trail runs at Sunset Bay State Park. Choose from four distances featuring cliffside ocean views, wooded paths, and beach sections in this RRCA sanctioned event.

A 5 km cross country race on a Tillamook flower farm featuring mud pits, two river crossings, wood-chipped trails and a corn maze. Two open races are held the same day with combined results and youth and adult categories.

Experience a premier alpine trail running event at Mt. Bachelor featuring four race distances that all peak at the 9000 foot summit. Enjoy volcanic scenery and rugged ridge lines in the heart of the Deschutes National Forest.

The inaugural Dragonslayer Fantasy Dash and Strut is a 5K event in Gabriel Park, Portland. Costumes are encouraged, and the course features Villain Zones. It welcomes walkers, runners, leashed dogs, and strollers.

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.

The Mook XC Invitational is a 5 km cross country race at The Mook at Alderbrook Golf Course in Tillamook, Oregon on September 19, 2026. The championship style course runs mostly on shortly clipped fairways and includes youth and adult categ..

Event Overview The Three Course Challenge is a cross-country event hosted by Seaside High School at Camp Rilea, just north of Seaside, Oregon. Since 1990, over 50,000 runners have participated. The event is described as celebrating the spor..