Trail Running calendar near Maupin 2025-2026

Run The Rock invites trail runners to tackle scenic single track around Smith Rock State Park near Bend with 50K and half marathon options. Support Ridgeview High cross country while enjoying aid stations and free shuttle parking.

Thunder River is a fall trail race in Cascade Locks, Oregon, with scenic river views and seasonal colors along the Pacific Crest Trail. Choose a 25K or 50K route that finishes at Marine Park after a loop around Thunder Island.

Experience a challenging 7 mile trail run from Dog Mountain Trailhead with sweeping views of the Columbia River, Mt Hood and Mt St. Helens. Expect a steep climb to the summit and a thrilling single track descent through the Gorge.

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..

Incline Vista on Cline Butte near Redmond OR offers sweeping Cascade and Smith Rock views. Pick a summit focused 20 mile challenge or a scenic 15K with runnable stretches and rocky sections for a memorable trail day.

Run among waterfalls and the dramatic Columbia River Gorge with 30K, 50K and 100K trail options from April 10 to 12, 2026. Expect marked courses, aid stations, camping nearby and a classic Pacific Northwest trail experience.

Run scenic ridge trails near Sisters, Oregon on April 12, 2026, choosing 20 mile, marathon, or 40 mile distances. Limited to 500 runners, the event benefits the Sisters High School cross country team and local trails.

Run scenic river and forest trails at Oxbow Regional Park with 5k, 10k and half marathon options on April 26, 2026. Limited to 150 runners, the cupless event features aid stations, post race food and an Oxbow cup for root beer floats.

Run the scenic single track trails around Sisters, Oregon with options of a 50K or Half Marathon. Enjoy Cascade peak views, post race food and beer, and support the Ridgeview High School cross country team.

Run Skull Hollow near Smith Rock with 50 mile, 50K and 10 mile courses on scenic single track and open grasslands. Finishers get awards, post race food and beer, and proceeds help a local high school cross country team.

Wild Woman Trail Marathon is a trail weekend created by and for women at the base of Mt Adams, with 50K, marathon, half and relay options on scenic forest trails. Enjoy camping at base camp, post run lunch and gentle yoga.

Wy'east Wonder is a point to point trail race around Mt Hood with 50 mile and 50K options along scenic ridges showcasing sweeping mountain and wildflower views. Start and finish at Red Barn Park with shuttles, awards and a finisher pint gla..

Choose from 50 miles, 50K, or 25K on shaded single track around Timothy and Clackamas Lakes with sweeping Mount Hood views along the Pacific Crest Trail. Friendly volunteers and a community vibe make this summer trail weekend memorable.

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.

Take on the Oregon Cascades 100, a point to point trail race in Oregon offering 100 and 50 mile courses across mostly single track, big climbs, and scenic forest roads. A Western States qualifier with custom buckles for finishers.

Run 100 rugged miles around Mt Hood in the Hood Hundred, a mountain trail ultra with epic views, heavy climbing and full crew support. Finish under 34 hours to qualify for Western States and earn a custom metal belt buckle.

Haulin’ Aspen is a mountain trail run in Bend, Oregon, through Deschutes National Forest with marathon, half and 6.5 mile options. Start and finish at Wanoga Sno Park as runners enjoy wooded single track, climbing terrain, aid stations and..

Wy'east Trailfest at Mt Hood Meadows on August 15 and 16 2026 features high alpine trail races. Distances range from a free kids run to a 50 miler with prize purses for select races, making it a must for trail runners.

The Post Canyon Half Marathon in Hood River, Oregon is a scenic and challenging trail half with big climbs, mountain views and creekside waterfalls. Expect rugged singletrack, supportive aid stations and unforgettable forest scenery.

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.