It’s almost impossible to cover all of Oregon  in a week, so we’ve crafted a 10-day tour that hits most of the highlights. Don’t take this itinerary too seriously—although we think it would be a great trip, don’t hesitate to stay longer at one site or discover your own favorite places along this route.
Also, since this is a “best of” tour, we haven’t gone the budget route; feel free to find less expensive lodging options in the travel chapters of this book.
With a mere 10 days to explore the entire state in this itinerary, we couldn’t quite get you into the heart of eastern Oregon, but that doesn’t mean we don’t highly recommend this part of the state. In fact, we like it so much we’ve devoted an entire itinerary to it .
Fly into Portland  and either pick up a rental car at the airport or take the MAX light rail train into town and arrange to get a rental car in downtown Portland. Spend the afternoon strolling around downtown, visiting Powell’s Books  and the Pearl District . Spend the night at the Heathman Hotel  and dine at nearby Higgins .
Head northwest out of Portland on U.S. 30 to Astoria . Explore this historic town at the mouth of the Columbia River, including a visit to the replica of Fort Clatsop , which served as Lewis and Clark’s winter home in 1805–1806. Then continue south and spend the night in Cannon Beach  at the Stephanie Inn .
Head south out of town on U.S. 101 and stop for a walk at Oswald West State Park , where you can follow the trail to Short Sands Beach  to watch the surfers. Continue down the coast as far as Yachats  and spend the night at Overleaf Lodge . Eat dinner at the Drift Inn .
Spend the morning exploring the tide pools and old-growth forest around Cape Perpetua . Take a tour of Sea Lion Caves  (or just peer down from the road with your binoculars). From the seaside town of Florence , cut east on Route 126 to Eugene , with a detour south to Lorane for a visit to the King Estate Winery  tasting room. Spend the night near Eugene’s riverside trails at the Campbell House B&B .
From Medford , just north of Ashland, drive up the Rogue River on Route 62  through the tiny towns of Prospect and Union Creek to Crater Lake National Park , where you’ll spend the night at the Crater Lake Lodge .
Hike along the Timberline Trail  (or spend the morning skiing—even in August) and then drive to Hood River . Take a hike to Upper Horsetail Falls  and then continue west to Troutdale, where you’ll spend your final night at the old county poor farm, now McMenamins’ Edgefield Lodge .