Trail Running calendar near Maupin 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.

Run stunning technical trails in the Columbia River Gorge at Gorge Waterfalls, a multi day race weekend in Cascade Locks with distances from 30K to 100K. Enjoy rugged singletrack, strong race support and benefit Trailkeepers of Oregon.

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..

Run along the scenic Sandy River at Oxbow Regional Park with 5k, 10k and half marathon options on rolling forest and river trails. Limited to 150 runners, this intimate spring trail event features aid stations, post race food and camping.

Spring trail runs in Sisters, Oregon on May 3, 2026 offer a challenging 50K or scenic half marathon on mostly single track trails. Proceeds support Ridgeview High School cross country and post race burritos and local beer celebrate finisher..

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 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.

The Wild Woman Trail Marathon will take place in Trout Lake from Saturday 20 June 2026 to Sunday 21 June 2026. You can run between 21 and 50 kilometers.

Strawberry Fields Forever in North Bonneville WA on June 20 features a scenic 10K loop on Strawberry Island with distances from 10K to 100 miles. Enjoy riverside forest views, steady aid, on site tent camping and easy access to Gorge attrac..

Take on a scenic but demanding point to point trail around Mt. Hood on June 27, 2026 in Parkdale, Oregon, with 50 miles or 50K options. Courses follow Gunsight Ridge and Surveyors Ridge and finish in the Hood River Valley for big mountain v..

Near Mt Hood, the Mt Hood Trail Runs offer 50 mile, 50K and 25K courses on scenic shaded single track and Pacific Crest Trail sections. Held over a July weekend with limited entries, finishers get a commemorative pint glass.

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.

Tackle the Hood Hundred, a 100 mile mountain trail race at Mt Hood Meadows with about 17,300 ft of climb and descent across rugged alpine terrain. A Western States qualifier with a capped field and a custom 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.

Wy'east Trailfest at Mt Hood Meadows on August 15 and 16, 2026 invites trail runners to tackle high alpine terrain and soak in epic mountain views on Saturday. Sunday features a half marathon, 8K and a kids race for runners of all levels.

Tackle the scenic Post Canyon Half Marathon in Hood River, Oregon, a challenging trail with roughly 2,300 ft of climbing, sweeping mountain views and creekside waterfalls. Cup free event with aid stations and finisher prize bags.

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 beneath the Three Sisters in Sisters, Oregon on scenic single track through pine forests, meadows and mountain streams. Choose a challenging 50K or a speedy half marathon and celebrate with a finishers medal and postrace burrito bar.