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..

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 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.

Experience Sisters Oregon trails on May 3, 2026 with a rugged 50K or a flowing half marathon, both starting and finishing at Village Green Park. Enjoy stocked aid stations, pre race coffee and a post race burrito bar and beer while supporti..

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.

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.

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.

Choose 50M or 50K and tackle rugged ridge top trails around Wy’east near Mt. Hood, finishing in the orchards of Hood River Valley. Expect big climbs, forest views and shuttles from Red Barn Park for a classic PNW trail experience.

Run scenic trails near Mt Hood on July 11 and 12 with 25K, 50K and 50 mile options using stretches of the Pacific Crest Trail and lakeside single track. Camp nearby and enjoy on course support and post race vibes.

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.

Run scenic singletrack and forest roads from Wanoga Sno Park in Bend, Oregon with marathon, half marathon or a 6.5 mile option. Expect rolling terrain, steep climbs, fast descents and great mountain views.

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.

Three Sisters Skyline in Sisters Oregon on September 19, 2026 offers a rugged 50K and a scenic half marathon that both finish in town. Run through Ponderosa pine forests, alpine meadows and along mountain streams for an unforgettable trail..

Tackle the Mountain Lakes 100 mile trail ultramarathon in the Oregon Cascades, starting and finishing at Olallie Lake Resort. Run about 60 miles on the Pacific Crest Trail through technical rocky terrain, alpine lakes and sweeping mountain..