Oregon is a big state, so don't expect to see it all in a week's vacation. However, if your vision of Oregon includes everything from forests of towering trees to snowcapped volcanic peaks and waves crashing on rugged shores, you're in luck: You can take in all of these, plus plenty of the state's famous wineries and brewpubs, during a 7-day visit--if you're willing to drive quite a bit. The following 1-week itinerary will allow you to experience many of the state's highlights.
Day 1: Portland
Start your visit in Portland, Oregon's largest city and a model of livability. Head to Washington Park to visit the Japanese Garden and the International Rose Test Garden. Hang out in a cafe, wine bar, or brewpub to find out how Portland relaxes. Ride the MAX or the Portland Streetcar (they're both free downtown) to visit some outlying neighborhoods. Wander around the Pearl District and stop by the Saturday Market if it happens to be the weekend. Stroll through Tom McCall Waterfront Park on the banks of the Willamette River, and then be sure to take a quick ride on the Portland Aerial Tram.
Day 2: The Mount Hood Loop
On your second day, head east from Portland through the Columbia River Gorge and around Mount Hood. In the Gorge, drive the Historic Columbia River Highway and try to avoid straining your neck while gazing up at Multnomah Falls and the gorge's many other falls. Take a short hike on the Eagle Creek Trail. Have lunch in Hood River, a town that has become one of the world's premier windsurfing and kiteboarding spots. As you loop around snowcapped Mount Hood, Oregon's tallest peak, stop at the historic Timberline Lodge. Go for a short hike through the wildflower meadows.
Day 3: Astoria
Next head west to the Oregon coast. Starting at the mouth of the Columbia River, you can explore Astoria, a historic river port and home to the Lewis and Clark National Historical Park. This town is still an active shipping and fishing port and has loads of character. Astoria's Columbia River Maritime Museum is one of the state's best museums. Don't miss it.
Day 4: Cannon Beach to the Three Capes Scenic Loop
The next day, head south from Astoria to Cannon Beach, the most charming town on the coast and home to the impressive Haystack Rock. Just north of town, visit the rugged beaches of Ecola State Park and south of town, stop at Hug Point and Arcadia waysides as well as Oswald West State Park. At this latter park, a short trail leads to one of the prettiest beaches in the state. Longer trails lead up onto rugged headlands. South of here, mellow out in Manzanita before continuing south to the Three Capes Scenic Loop, which takes in Cape Meares, Cape Lookout, and Cape Kiwanda.
Day 5: Newport
Continue driving south, through miles of traffic congestion in Lincoln City, to Depoe Bay, where you'll find not only the smallest natural harbor on the coast but also, south of town, the Otter Crest Scenic Loop and Devil's Punchbowl State Natural Area. Continuing south you'll come to Newport, my personal favorite of the coast's family-vacation destinations. The big attraction here is the Oregon Coast Aquarium. On the Newport Bayfront, you'll find both fish-packing plants and souvenir shops. Here in Newport, you can also visit the Yaquina Bay Lighthouse and the Yaquina Head Lighthouse.
Day 6: Crater Lake National Park
Today is your longest drive, so get an early start and spend some time at Cape Perpetua Scenic Area, Heceta Head Lighthouse State Scenic Viewpoint, and Sea Lion Caves. Head inland at the historic river town of Florence, perhaps after grabbing some lunch on the town's historic waterfront. Follow the beautiful blue waters of the North Umpqua River from Roseburg to Crater Lake National Park. If you reach the national park early enough, drive the scenic road that circles the lake.
Day 7: Ashland
This morning, take a boat tour on Crater Lake, then head down out of the mountains to the town of Ashland, which is the home of the Oregon Shakespeare Festival. It runs from February to October and is the state's premier performing-arts festival. Ashland has loads of great shops and restaurants. The next day, either drive back to Portland or fly out of Medford.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.