Trail Running calendar near Maupin 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.

Challenge yourself on scenic trails through the Columbia River Gorge in Cascade Locks with 30K, 50K and 100K options. The 100K is a Western States qualifier and all races carry a UTMB Index, with proceeds benefiting 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 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.

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.

Wild Woman Trail Race Weekend is a women focused trail running retreat near Mt Adams in Trout Lake offering distances from half marathon to 50K plus relay options. Camp at base camp, run scenic forest and field trails, and enjoy lunch and p..

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..

Tackle the Wy’east Wonder, a scenic point to point trail race on Mt Hood offering sweeping ridge views and net downhill miles. Choose the 50 mile or 50K for a rugged, unforgettable day on Gunsight and Surveyor's Ridge.

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.

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..

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.

Wy’east Trailfest is a two-day mountain event at Mt. Hood Meadows on August 15 and 16, 2026, featuring alpine trails to 8,000 feet and distances from a kids run to 50 miles. Expect marked courses, full aid stations, camping and custom finis..

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.

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.