Oregon
Oregon Trail Running Calendar 2026-2027
Explore the best trail runs in Oregon for 2026-2027! Our updated list features 96 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
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
Perpetua Coast is a trail race weekend in Yachats, Oregon on October 3 and 4, 2026 offering 50K, 20 mile, half marathon and 10K courses along Cape Perpetua coastal trails.
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.
A 25K trail race in Corvallis on October 4, 2026, starting at OSU Peavy Arboretum, with proceeds supporting local trail work, rescue, and a shoe assistance program.
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.
A virtual Indigenous Peoples Day run with 5K, 10K and half marathon options, in-person 5K meetups in Portland and Seattle, and fundraising for three beneficiaries.
Trail race at Whiskey Run Trailhead on Oregon's Adventure Coast with shaded single track loops of 1.5, 5, and 10 miles.
Trail races in Rainbow OR offering 50K and 20K routes with extensive climbing, multiple aid stations, drop bag support, and post-race food at the community center.
Dogwood Dash is a charitable 5K on October 10 at North Clackamas Park with proceeds split between LoveOne and the Corporal Diffie Veterans Fund.
A nighttime family friendly 5K in Downtown Dallas OR with a glow theme, costume contest, Kid's Dash, event items, and fundraising for local nonprofits.
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.
Three days of trail races at Silver Falls State Park offering 5K, 7 Miler, Half Marathon, Marathon and 50K with registration open Aug 1 to Oct 10, 2026.
Weekend trail races on October 17 and 18, 2026 along the Upper Rogue River featuring point to point 50 Miler and 50K plus loop Half Marathon and 12K.
Experience the technical trails of the Tillamook Forest with a steep 25K summit run, a scenic 50K along the Wilson River, or a new 11 mile point to point course.