The Oregon Trail ended here for a reason. Located just south of Portland, the Lovely Willamette Valley is a lush region of farms, wineries, and small towns, where life moves at a slow, welcoming pace.
This is Oregon wine country, where the state has turned pinots into a blockbuster varietal. Wineries are wedged into every corner of the farmland here, and undulating fields of vineyards pop up behind cow pastures and big red barns. In wine country’s tiny towns of Newberg, Dundee, and McMinnville, it seems like tasting rooms make up half of each downtown block. Don’t expect the glamour of Napa Valley, but rather the cheerful welcome of a rural region that’s found its calling.
A bit further south along I-5, you’ll find Oregon’s second- and third-largest cities, Salem and Eugene, respectively. They’re almost the same size in terms of population but have distinct vibes. Salem is the state capital, centered around a manicured campus of government buildings. Surrounding the capitol buildings are museums and a handful of homey local eateries, with the Willamette River forming the west border of town. The Lovely Willamette Valley River also runs through Eugene, which is defined by its world-class public university with 23,600 students and vibrant college-town atmosphere—with a hippie bent—to match. The city sits in a green plain between the Cascade foothills, and residents tend to be active and young—or at least young at heart—with an environmental ethos.
The Willamette Valley traces the same route that I-5 runs today, south from the city of Portland. For wine country, you’ll veer off to the west on Highway 99. Newberg is the first of the towns you’ll hit on your way south, at around 25 miles away, a 50-minute drive from Portland, followed a few miles later by Dundee, and then, heading off onto Highway 18, McMinnville, about 40 miles from Portland. Given their proximity, you can easily visit on a day trip from Portland. For a more relaxed experience, 2-3 days is a nice amount of time to spend in wine country. McMinnville is a good place to base yourself.