Trail Running calendar near Maupin 2026-2027

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 Incline Vista near Redmond OR on Cline Butte for sweeping views of the Cascades, Smith Rock and the Ochoco Mountains. Pick a challenging 20 mile with big climbs or a scenic 15K with runnable and rocky sections.

Gorge Waterfalls trail runs Apr 10 to 12, 2026 in Cascade Locks along the Columbia River Gorge, offering 100K, 50K and 30K. The 100K is a Western States qualifier and all distances are UTMB Index races.

Run the scenic Peterson Ridge Rumble near Sisters Oregon on April 12, 2026 with 40 mile, marathon and 20 mile trail options. Limited to 500 entrants, dog friendly, and supporting Sisters High School cross country and local trails.

Run scenic river and ridge trails at Oxbow Regional Park near Portland on April 26, 2026, with 5k, 10k, and half marathon options. Limited to 150 runners, this trail race offers unique awards and a commemorative Oxbow cup.

Enjoy spring trail running in Sisters, Oregon on May 3, 2026 with 50K and half marathon courses that showcase views of the Three Sisters. After the race enjoy burritos, beer and medals while supporting Ridgeview High School cross country.

Explore Smith Rock country from Skull Hollow with 50 Mile, 50K or 10 Mile options amid basalt cliffs and Cascade Range views. Tough single track courses benefit Ridgeview High School and finish with a post race burrito bar.

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.

Join Wild Woman Trail Race Weekend in Trout Lake at Mt Adams for a women's trail running escape with 50K, marathon, relay and half marathon through fields and forests. Camp at basecamp then enjoy post run lunch and yoga with fellow runners.

Run scenic loops on Strawberry Island in the Columbia River Gorge through fields, forest, and river views. Distances from 10K to 100 miles, with aid stations, food, and a lively finish at North Bonneville Ball Fields.

Run along Mt Hood ridgelines from Parkdale to the Hood River Valley in Wy'east Wonder, a scenic point to point trail race offering 50 mile, 50K and a two person 50K relay. Expect ridgeline singletrack, big net downhill and orchard finishes.

Explore scenic trails around Timothy Lake and Mt Hood with 25K, 50K and 50 mile options largely on the Pacific Crest Trail. Enjoy soft but sometimes technical singletrack, full aid and a commemorative Mt Hood pint glass at the finish.

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.

Oregon Cascades 100 delivers rugged, scenic point to point trail racing through central Oregon to Sisters, offering 100 and 50 mile options. Challenging single track, full aid support, and Western States qualifying glory await.

Climb the trails at The Hoodoo Challenge: Run To The Top in Sisters, Oregon on July 25, 2026, with half marathon and 5K options offering panoramic forest and summit views. Enjoy a hosted lunch, awards and proceeds supporting local charity.

Hood Hundred is a challenging 100 mile mountain trail race on Mt Hood with roughly 17,300 ft of ascent and descent across a scenic lollipop loop. It is a Western States qualifier with a 34 hour cutoff and rewards finishers with a custom met..

Tackle single track trails in Deschutes National Forest at Wanoga Sno Park for the 22nd Haulin' Aspen with marathon, half and 6.5 mile options. Enjoy a post race party with music, food, beer and vendors while supporting Bethlehem Inn.

Wy’east Trailfest at Mt Hood Meadows on August 15 and 16, 2026 is a weekend of alpine trail racing from kids runs to a 50 Miler, climbing to 8,000 feet. Expect marked courses, full aid, chip timing, pro photos and a lively finish festival.

Experience the Post Canyon Half Marathon in Hood River Oregon on August 22 2026, a scenic trail race with waterfalls, mountain views and roughly 2300 ft of climbing. Enjoy aid stations, finisher swag and a lively trail atmosphere.

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.