Day 4

Follow our suggestions for days 1 to 3, and then rent a car for your final 2 days in Portland so you can see some of the state’s magnificent scenery. On day 4, head east out of town on I-84. The spectacular Columbia Gorge begins just a few miles east of downtown. For the most scenic drive, take the Columbia Gorge Historic Highway—we just call it “the Old Gorge Highway”—the first scenic road to be built in Oregon back in the 1920s, with bridges and walls constructed by Italian stonemasons. The old highway takes you up to Crown Point, where the breathtaking view extends for over 30 miles.

Continue on the old highway and you will pass a handful of sparkling, rushing waterfalls until you come finally to the tallest and most dramatic waterfall of all—Multnomah Falls, one of the highest waterfalls in North America. Have lunch at historic Multnomah Falls Lodge.

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At this point you can jog back to I-84, the faster and newer highway that runs closer to the river. (Please note, however, that a wildfire in September 2017 charred part of the forest in the Gorge.) From here, you can head south and continue your expedition by driving up and over Mount Hood. Timberline Lodge is one of the greatest alpine lodges ever built; inside and out it is a rugged yet sophisticated creation of the Works Progress Administration under Franklin D. Roosevelt in the 1930s. You can have a coffee or dinner at the lodge, or return to Portland, about 2 hours away.

Day 5

Oregon is famous for the quality of its wines, particularly pinot noirs. Vineyards are scattered throughout the western part of the state—west of the Cascades, that is—but the ones closest to Portland are in the North Willamette Valley. Have a look in chapter 5 at the day trip called “The Wine Country,” and head into the rolling hills of the valley to visit and taste wine at some of the outstanding vineyards there. And you can reach the Valley in about an hour, if the traffic gods are with you.

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Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.