Cycling & running events in Portland, 2026

Portland Base Miles And Hills

Running: Locals run Forest Park when they want real trail time without leaving town. Forest Park covers over 5000 acres and 70 miles of trails, so Wildwood Trail, Leif Erickson, roots, rocks, and Z2 all fit in one week. The waterfront gives easy miles from Sellwood to Steel Bridge, and the Steel Bridge to Sellwood Bridge loop runs 10 miles almost entirely off road and by the river. Portland Running Company, No Name Trail Club, Trail Factor, Team Red Lizard, Deadstock Run Club, and Rose City Run Club keep the calendar full. Portland Marathon, Shamrock Half-Marathon Portland, Starlight Run, and Hood to Coast are the anchor events.

Cycling: Locals ride everything from flat river miles to punchy West Hills climbs. Portland Velo Cycling Club and Portland Bicycling Club run group rides, with Portland Velo doing weekly rides and the Saturday Signature Ride starting from Hillsboro. The West Hills, Germantown Road, Skyline Boulevard, Council Crest, Rocky Butte, Powell Butte, and Mt Tabor are where the climbing legs get made. The Banks-Vernonia trail gives paved base miles, and the CZ Trail runs gravel from Scappoose to Vernonia. Tualatin Valley - Woodland Loop Metric packs 579 m of gain into 106 km, and Hills & Rollers on Hillside gives 505 m in 73 km.

Season: Summer months are the sweet spot because the trails are almost never crowded and Forest Park stays way cooler than baking on the pavement. Locals use those months for long runs, base miles, Springwater Corridor out to Boring, Marine Drive to Blue Lake Park, and Washington County rollers through Forest Grove, North Plains, Gaston, and Cornelius. October brings harder rain, and winter shifts the routine toward lights, fenders, rain gear, and more lunch-hour riding. Runners still hit Duniway Track, the waterfront, Forest Park, and Powell Butte, while dedicated cyclists keep riding unless snow or ice shows up.