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!
A crew-friendly 100-mile ultra at Stub Stewart State Park, Oregon, with about 7,000 ft gain, a 2-person relay option, and a Royal Purse funded by a 10% registration tax.
Multi-distance trail race on a 6.5 mile loop at L.L. Stub Stewart State Park where runners choose their distance on race day.
May 2027
A 57 mile running relay in Central Oregon featuring 12 legs, scenic river views, and craft beer samples from local breweries at exchange points and a finish line festival.
Trail 50K and Half Marathon in Sisters, Oregon on May 2, 2027, start and finish at Village Green Park with aid stations, post race food, and finisher medals.
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.
A Seriously Fun 5K obstacle run at Moto541 in Central Point, Oregon on May 8, 2027, open to all ages with required signed waivers and a spectator festival option.
A women-focused running event in Bend offering a half marathon, 10K, 5K and a kids run, with aid stations, gear drop, post-race vendors, and a community beneficiary supporting outdoor access for youth of color.
A time trial on Firelane 1 in Forest Park covering 4.45 miles with 1,266 feet of gain and loss, wave starts at ten minute intervals and a post race gathering at Great Notion Brewing.
A spring trail weekend in Oregon’s Tillamook State Forest featuring a point-to-point 50 mile and a 55K lollipop course staged at Reehers Camp.
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.
Overnight and day loop racing at Cline Buttes with 3/6/12/24-hour options, a Last Person Standing format, and a 5k on a 3.1 mile loop with a steep climb.
Trail races of 50 mile, 50K, and 10 mile around Smith Rock State Park featuring basalt cliffs, Crooked River Grasslands, and Cascade Range views.
Trail races in Portland's Forest Park over Memorial Day weekend featuring the city's only 50K and a hilly trail half, with proceeds benefiting the Forest Park Conservancy.
June 2027
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.
Trail and virtual races June 5 to 6, 2027 at Clackamas Lake Historic Ranger Station Oregon, featuring a 25.2 mile marathon, 14 mile half marathon, and views of Mt Hood.
Loop trail races on Cape Mountain near Florence OR featuring 50K, 25K and 10K courses through old growth forest, creek canyons and coastal meadows.
Test your limits at Elijah Bristow State Park with 6, 12, or 24 hour timed challenges on a flat one mile trail loop.
Uphill trail event June 6, 2027, about 13.5 miles from Lithia Park to the Mt Ashland summit with over a mile of elevation gain; proceeds support local trail nonprofits.
Trail races on Marys Peak in Blodgett, Oregon on June 12, 2027 offering 50K and 25K routes up to the summit with marked trails and aid stations.