Trail Running calendar near Rainbow 2025-2026

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.

Run for the Oaks is a scenic trail day at Left Coast Estate with 5K and 10K routes through vineyards and old growth oak savanna. Finish with wine tasting, live music, and help fund oak restoration.

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.

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 through Ponderosa pines, alpine meadows and mountain streams in Three Sisters Skyline, a scenic trail race near Sisters, Oregon with 50K and half marathon options. Both courses finish in town and benefit the Sisters Trail Alliance.

Mountain Lakes 100 is a scenic 100 mile trail race at Olallie Lake Resort, running between Mt Jefferson and Mt Hood with long stretches on the Pacific Crest Trail. Expect technical single track, big mountain views and a 150 person field.

Join the new Oxford Classic Community 5k in Bend on Saturday, October 3, 2026, for a scenic loop at Drake Park along the Deschutes River. Flat, wide paths make it perfect for all abilities and family spectators.

Run through lush forests and waterfalls at the 16th annual Silver Falls trail races in Silverton Oregon on Saturday October 17 2026. Choose from a 50K, marathon or 7 miler with limited entries opening August 1 2026.

Run The Rock invites trail runners to tackle scenic single track around iconic Smith Rock and high Cascade peaks near Bend, Oregon. Choose a 50K for big climbs and views or a half marathon for a spirited taste of the same terrain.