With 10 days, you can get a taste of Oregon’s largest city, eco-conscious Portland, while also getting a nice sense of the state’s geographical diversity—the mountainous and sweeping coast, gorgeous Crater Lake, the rugged Cascade Mountains, and the eastern high-desert regions.
Days 1 and 2: Portland
Start by spending a couple of days in Portland, where you can tour the museums and attractions that make up Washington Park, as well as the Lan Su Chinese Garden in Old Town, and the excellent museums and cultural institutions along Downtown’s leafy Park Blocks. This city of vibrant, distinctive neighborhoods offers plenty of great urban exploring, with Nob Hill, Hawthorne District, Alberta Arts District, and North Mississippi Avenue among the best areas for shopping, café-hopping, and people-watching. If you have a little extra time, consider spending a couple of hours just south of the city in the Willamette Valley Wine Country, an easy jaunt from Portland.
Days 3 and 4: Oregon Coast
(1½ hours by car from Portland to Cannon Beach)
Leave Portland early on Day 3 for the drive northwest about 100 miles on U.S. 30 to the small city of Astoria, which has several excellent spots for lunch and the Columbia River Maritime Museum. Pick the main scenic highway down the Oregon Coast, U.S. 101, and continue south, stopping at Fort Stevens State Park and Fort Clatsop in Lewis and Clark National Historic Park. End the day in charming Cannon Beach (26 miles south of Astoria), which has a wealth of oceanfront hotels and inns, many with views of one of the region’s seminal features, 235-foot-tall Haystack Rock. Be sure to check out the stunning beach scenery at nearby Ecola State Park and Oswald West State Park.
The following morning, continue south down U.S. 101. In Tillamook (famous for its cheese), take a detour onto the Three Capes Loop, a stunning 35-mile byway. Stop in small and scenic Pacific City (at the south end of the loop) for lunch. Once you’re back on U.S. 101, continue south to Newport, spending some time at the excellent Oregon Coast Aquarium as well as Oregon State University’s fascinating Hatfield Marine Science Center. Your final stop is the charming village of Florence, 160 miles (about four hours by car) from Cannon Beach.
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Day 5: Eugene
(2½ hours by car from Florence to Eugene with detour at Oregon Dunes)
Spend the morning driving 20 miles south of Florence along U.S. 101 to scamper about the sandy bluffs at Oregon Dunes National Recreation Area near Reedsport. Then backtrack to Florence for lunch in Old Town before taking Highway 126 east for 60 miles to the attractive college city of Eugene, staying at one of the charming inns or bed-and-breakfasts near the leafy campus of the University of Oregon. Take a walk to the summit of Skinner Butte in Skinner Butte Park, which affords fine views of the city, and plan to have dinner at one of the top-notch restaurants at the 5th Street Public Market. Budget some additional time in Eugene the following morning to visit two excellent museums at the University of Oregon, the Jordan Schnitzer Museum of Art and the Museum of Natural and Cultural History.
Days 6 and 7: Crater Lake and Ashland
(3 hours by car from Eugene to Crater Lake National Park or Prospect)
From Eugene, take Interstate 5 south for 75 miles to Roseburg, then head east along Highway 138 (the Umpqua River Scenic Byway), which twists and turns over the Cascade Range for 85 miles to the northern entrance of Crater Lake National Park. Once inside the park, you can continue along Rim Drive for another half hour for excellent views of the lake. Overnight in the park or in nearby Prospect.
The following morning, take the lake boat tour to Wizard Island and hike through the surrounding forest. In the afternoon, head southwest on Highway 62 to Interstate 5, then continue on to Ashland, 95 miles (about two hours) from Crater Lake. Plan to stay the night in one of Ashland’s many superb bed-and-breakfasts. Have dinner and attend one of the Oregon Shakespeare Festival productions (April through October).
Days 8 and 9: Bend
(3½ hours by car from Ashland)
Get an early start out of Ashland, driving east along scenic Highway 140, which skirts picturesque Upper Klamath Lake, and then north on U.S. 97 to reach the outdoorsy resort town of Bend. Here you can spend two nights checking out the parks, mountain hikes, microbreweries, and restaurants of the state’s largest city east of the Cascades. Be sure to visit the outstanding High Desert Museum, the Old Mill District, and Mt. Bachelor, an alpine ski resort area.
Day 10: Hood River
(3 hours by car from Bend)
From Bend, continue north up U.S. 97, and then northwest up U.S. 26 to Mt. Hood, 105 miles total. Have lunch at the historic Timberline Lodge, admiring the stunning views to the south of the Cascade Range. Pick up Highway 35 and drive around the east side of Mt. Hood and then north 40 miles to the dapper town of Hood River, in the heart of the picturesque Columbia Gorge. Spend the night at one of the attractive inns, and try one of this town’s stellar restaurants for dinner. From here it’s just a 60-mile drive west along a scenic stretch of Interstate 84 to reach Portland.