Distance from Portland: 170 miles, 3.20-hour drive
Why it made our list: It's one of the most scenically diverse road trips in the state, traversing Mt. Hood National Forest, petrified forest, desert canyons, and lava lands. And who's the real beer capital of Oregon anyway? Bend has more than 30 breweries, along with every outdoor activity on Earth, including cycling the Bend Ale Trail and floating the Deschutes River to Mirror Pond.
Pro tip: On the way there, take the more travel road, Route 26, but on the way back, take Routes 20 and 22. This route runs through Deschutes National Park, Mt. Jefferson, and the bizarre, tree-stump-studded Detroit Lake. Did you know that creating the lake flooded a town? Not long ago, you could still see the tops of the buildings sticking out.