Craggy coasts, vast volcanoes, lush vineyards, remote forests…it’s hard to match the geographical diversity of Oregon, making the Beaver State a cherished road trip destination.
Start in eclectic Portland, where quirky meets classy in a delightful blend that’s just as rich as a Willamette pinot noir. Attend a Portland Timbers match and scream with the supporters, then take a load off at a laid-back East Portland hipster dive like McMenamins Kennedy School, a former school-turned millennial party palace.
The next day, it’s time to explore – and we’ve got a packed schedule for you. Hit the road toward towering Mount Hood, which presides over Northwest Oregon from its pulpit 90 miles outside town. On your way, stop in the pastoral town of Sandy for a blueberry fritter from Joe’s Donuts – you won’t miss the red-and-white-checkered building. Cross the street for a coffee from Mountain Moka, then hop back on Highway 26 toward the mountains.
Mount Hood stands at 11,250 feet, but your first date with the mountain should be in the valley below. Bear right toward Trillium Lake and take a quiet walk around the water until you catch Mount Hood’s reflection in the glassy surface. You won’t find a better picture spot. Then drive back up the hill and head to Government Camp, a pocket-sized tourist town on the side of the slope. It’s home to several shops, restaurants and boutique hotels; you can also hit trails that’ll get you up the mountain.
Down the highway is the entrance to Timberline Lodge, a steep and winding road that’ll take you up to 6,000 feet. If you’re going in fall or spring, use all-weather tires to counter the wildly unpredictable weather at that altitude; if you’re going in winter, only winter tires will suffice.
When you’re ready to head down the mountain, veer east on the highway. It weaves around the other side of the volcano, offering fresh glimpses and new picture angles for your passenger. The road eventually takes a northern heading toward the Columbia River. When you’re a few miles away and encounter the town of Odell, look for Wy East Vineyards on the right side of the road. Responsibly sip the vivid, fruit-forward flavors of Oregon grapes on the sun-splashed patio.
Now it’s time for your journey to take its final – and maybe most exciting – stage. When Highway 35 forks into I-84 at the Columbia River, head west toward Portland. You’ll snake your way 60 miles back to town, but not before encountering several stunning waterfalls cascading into the gorge. Highlights include Multnomah Falls, Bridal Veil and Latourell Falls.
When you’ve had your fill, mosey back to Portland for dinner and drinks at Deschutes Brewery. If you’re interested in more exploration, head to the coast the next day, stopping at world-famous Tillamook Creamery on your way. Here’s that route for your consideration.