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 entirely different itinerary to it.
Fly into Portland International Airport 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 Restaurant & Bar.
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.
Drive south along I-5 to Ashland to attend a world-class play. Dine at New Sammy’s Cowboy Diner (reserve well in advance) or Amuse, and spend the night at the Ashland Springs Hotel.
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.
Head north on U.S. 97 to Bend, visiting the Lava Lands Visitor Center and High Desert Museum on the way. Stay downtown at the Oxford Hotel or a few miles out of town along the Deschutes River at the Seventh Mountain Resort.
Continue north to Maupin to meet your raft guide for a daylong float down the Deschutes. At the end of the day, drive up Mount Hood and spend the night at Timberline 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 McMenamins’ Edgefield Lodge, once the county poor farm.
It doesn’t take long—about 20 minutes—to get from Edgefield to the Portland airport. If you have a late flight, spend the day in Portland, visiting Washington and Forest Parks.
Excerpted from the Ninth Edition of Moon Oregon.