Oregon
Oregon Trail Running Calendar 2026-2027
Explore the best trail runs in Oregon for 2026-2027! Our updated list features 103 exciting trail runs across the region. Find your next trail run in Oregon below and join the trail community at these great events!
September 2026
A cross country meet at Camp Rilea near Seaside Oregon on September 26, 2026, featuring four flagged courses, chip timing, team lodging, and weekend meals.
Trail event on September 26, 2026 offering 23 mile, half marathon, 11K and 7K courses on single track and forest roads; proceeds support local youth sports.
A cross-country event in Talent, Oregon featuring a community 5K and a free elementary mile; proceeds support Talent Middle School Cross Country.
Experience a scenic run along the Santiam River in Stayton with 10k, 5k, and 3k options featuring a mix of pavement, gravel, and trail.
A 3.1 mile obstacle run with 22 symbolic obstacles raising funds and awareness for organizations that combat human trafficking and support survivors.
Second annual trail race at Teacup Ski Trail System on Sept. 26 with distances from 1.3 km kids to 7.5 km across mixed single track, road, and two track terrain.
Community running day at Willamette Mission State Park on Sept 26, 2026 with chip timed 5K and 10K plus accessible All Abilities loops and post-race pancakes.
Trail races at Moore Park in Klamath Falls on September 26 2026 offering 30K, half marathon and 5K mostly on single track with lake and mountain views.
A four-race fall cross country series in Portland with separate men's and women's races, USATF championship events, and both series and single-race registration options.
An end of summer coastal trail race at South Beach State Park offering 5K, 10K and half marathon distances with mixed surfaces and aid stations.
Low-key evening trail series in Forest Park with three five race seasons, 4 to 7 mile courses, standings for regular participants, and a post season awards party.
October 2026
Trail races in Yachats, Oregon, through Cape Perpetua’s coastal bluffs, beaches and old growth rainforest with distances from 6.2 to 31.0686 miles.
A last person standing trail race on Hamilton Island in the Columbia River Gorge where runners repeat a 4.13 mile loop each hour and must finish each loop in under 60 minutes to continue until one runner remains.
35th OXFORD Classic Community 5K in Drake Park, Bend, is a flat riverside loop open to all ages with free registration.
Mountain trail races on Mount Bachelor over October 3–4, 2026, including 6/12/24-hour summit loops and three looped courses. Chairlift use is included and multiple aid stations and lodge facilities support runners on alpine singletrack.
Community races at Scappoose High School on October 3 offering a 5K and 1K on grass and track with proceeds benefiting the high school cross country program.
Experience a scenic autumn tradition in Bend with downhill courses and riverfront views. Choose between a half marathon, the historic Bigfoot 10k, or a family friendly 5k through the Old Mill district.
Experience the trails of the Peavy Arboretum in Corvallis at the Condor 25K Trail Run a non profit race benefiting local trail building and rescue units.
In-person event in Gresham on October 4, 2026 with a 5K, a kids dash for ages eight and under, and a virtual run option.
Backwoods 5k in Hillsboro is a 3.1 mile loop on October 4, 2026 supporting child meal access, with awards and a commemorative pint on the Backwoods rooftop.