Oregon is a tale of the outdoors. It is a land of both grand and intimate landscapes, from the widest desert vistas to the tiniest tide pools. It is a place where residents’ time is measured not by meetings nor to-do lists, but by the length of bike track left in the mud, the miles of shoreline paddled, the layers of dirt caked high on hiking boots. The vast wilderness, from coast to countryside, presents the perfect conditions for dreaming while awake, for creativity needs space to flourish. The resulting Oregonian ingenuity drives not only a way of life, one of self-reliance and fierce preservation of the environment, but much of the beer, wine and food world, too. Which is why a long, slow drive across this sparsely-populated state is one of America’s last great road trips. With excellent road conditions largely devoid of cars but rife with wilderness, wineries and breweries, you may just want to stay forever.
While the following itinerary took 10 days to complete, the pace was admittedly relaxed. Driving a figure-eight, all journeys begin in Portland before heading south to Willamette wine country. After a few days of tasting Pinot, Riesling (and beer!), push on through Mt. Hood to the lakes, forests and breweries of Central Oregon and Bend. Circling up past Smith Rock and the high desert, spend a night in the city before departing for the coast. Starting north in Astoria, known as “little SF,” skirt the ocean down 101 past Cannon, until alighting on Pacific City. You’ll take in restaurants serving fresh-caught seafood — or attempt to catch your own — all paired with local beer, wine, and lots and lots of coffee.
While this missive extolls the virtues of this Pacific Northwest state, it does not advocate for making a reckless move west based on one joyful road trip. Committing to a relocation while in the throes of a summer romance is like marrying a new lover after a wild weekend fling. Oregon’s summers are seductive. It’s easy to fall in love. But they’re short.
June through September is the best time to visit if…