Trail Running calendar near Cougar 2026-2027

The Long Watch is a 6 hour, 12 hour and 24 hour loop endurance event at Donald Farm in Woodland, Washington, held alongside the Warrior Expo, with a manned aid station and a one mile loop past competition and vendor areas.

A point to point **50K** on the Pacific Crest Trail from the South Washington Cascades into the Columbia River Gorge, including a detour to the Three Corner Rock viewpoint. Proceeds benefit the Stevenson High School Cross Country Team and t..

A Portland event offering a 50K and a longer roughly 53 mile option. The mostly paved course includes a steeper one mile trail section, is unsupported, and uses GPX files rather than course markings.

A low-key evening trail running series in Forest Park, organized as three Series of five races with courses around 4 to 7 miles. The Series includes standings, a post-Series awards gathering, and benefits the Forest Park Conservancy.

Cirque Series at Crystal Mountain is a 7.9 mile trail race with 2,614 feet of vertical gain on September 19, 2026. Sport, Expert and Pro divisions offer prizes and series points, and timing is by disposable bib chip.

The Three Course Challenge is a cross country meet at Camp Rilea north of Seaside, Oregon on September 26, 2026. It features multiple middle and high school courses, chip timing, team lodging, live drum corps performances, and awards.

A 3.1 mile obstacle course featuring 22 symbolic stations that represent the journey from captivity to liberation. Proceeds support the Path to Freedom Project and organizations that assist survivors of human trafficking.

Mission Possible at Willamette Mission State Park on 26 September 2026 offers chip-timed 5K and 10K trail races plus accessible All Abilities 2.25-mile and 1.6-mile loops, with volunteers on course and post-race pancakes and snacks.

A five-race cross country series in Portland parks with separate men’s and women’s races, options for non-binary entrants, race distances of 5K 6K and 8K, and both series and individual registration fees.

A trail running event at Teacup Ski Trail System on Sept. 27 with a new course and three distances, including youth and kids races. The route features lake views, varied terrain, one water station, and on-site parking and restrooms.

A low-key evening trail running series in Forest Park, organized as three Series of five races with courses around 4 to 7 miles. The Series includes standings, a post-Series awards gathering, and benefits the Forest Park Conservancy.

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.

A last-person-standing backyard ultra on October 3rd, 2026 where a $100 bill is added to the prize jar each lap; the winner and runner-up split the accumulated pot 75/25 and 24 laps earns a 100-mile buckle.

An in-person and virtual event on October 4, 2026 in Gresham featuring a 5K, a kids dash for ages eight and under, and a virtual run/walk. Registration opens in April and fees vary by event.

A low-key evening trail running series in Forest Park, organized as three Series of five races with courses around 4 to 7 miles. The Series includes standings, a post-Series awards gathering, and benefits the Forest Park Conservancy.

A multi-distance loop event on October 24, 2026 near St. Paul, OR, featuring 50 mile, 50 km, 30 km and a free 1 km kids run on a mostly paved, flat 10k loop with aid stations and a cupless policy.

A fall-themed running event at Pacific Community Park with youth races and an open 5k on mostly grass and compact trail. Medals go to the top 15 in each race and the top boy and girl receive a Halloween blanket.

A low-key evening trail running series in Forest Park, organized as three Series of five races with courses around 4 to 7 miles. The Series includes standings, a post-Series awards gathering, and benefits the Forest Park Conservancy.

A trail race day on October 31, 2026 in Cascade Locks, Oregon featuring a 25K point to point and a 50K lollipop course along the Pacific Crest Trail and Gorge 400 trail, finishing at Marine Park with aid stations, timing, and post race awar..

A nonprofit trail event in Klickitat, WA, featuring a half marathon and 5K along the Klickitat River, shuttle access to trailheads, aid stations, post-run chili with a vegetarian option, and awards for top finishers.