Where to Go

Oregon [1] is a large state with plenty to keep a visitor — or an Oregonian with wanderlust — on the road for weeks. Realistically, however, you probably need to plan your trip based on the time you’ve carved out for it.

A Long Weekend

Use Portland [2] as a hub and make the most of excursions out into the wilds by day while enjoying the city’s sophisticated dining and cultural scene by night. Some of Oregon’s top sights and experiences are just 1.5 hours from the city center.

The northern Oregon coast [3] and the Yamhill County wine country [4] can be combined into a day trip: lunch at the beach, wine tasting in the afternoon, and back to town in time to take in a play or concert with a late-night dinner to follow.

The most iconic of all day trips from Portland loops through the Columbia Gorge [5] and its dramatic waterfalls, then up and around Mount Hood [6], the state’s highest peak. And you’ll want at least part of a day to explore cosmopolitan Portland’s quirky sights — gardens, burgeoning arts and crafts markets, and tax-free shopping will make the time fly.

One Week

Spend a day or so in Portland [2], then drive the northern Oregon coast, spending a night in Astoria [7] or Cannon Beach [8]. Follow coast-hugging U.S. 101 south to Newport [9], with its world-class aquarium, then turn back inland and cross the Willamette Valley [10] (with stops to taste wine highly encouraged) and traverse the Cascades to Bend [11], a resort community at the point where mountain forests meet high desert.

Spend a couple of days exploring alpine lakes, volcanic oddities, river canyons, and Bend’s youthful outdoor-oriented spirit. Then take the slow road back to Portland, following the Deschutes River and cutting up to Mount Hood [6], where you’ll spend the night at historic Timberline Lodge [12] before driving on for another day’s exploration of Portland.

Two Weeks

You’re lucky, because you’ll have time to journey through little-explored but scenically wondrous eastern Oregon and also extend your trip to the highly dramatic southern Oregon coast. Leave Portland [2] via the Columbia River Gorge [5] and head to the Willowa Mountains, a range of lofty lake-jeweled peaks at the edge of the continent’s deepest river canyon, the Hells Canyon of the Snake River. Continue south to Oregon’s outback, where desert lakes at Malheur and alpine meadows on Steens Mountain are just the beginning of the area’s startling incongruities.

Head west to Bend [11], take a day to play golf or white-water raft, then head south to uncannily blue Crater Lake [13], the state’s only national park and the deepest lake in the United States. From here it’s a short drive down the Rogue River to Ashland [14], home of the Oregon Shakespeare Festival [15] and center of a burgeoning wine-producing area.

From Ashland, a half-day’s drive takes you to the southern Oregon coast [16], surprisingly unthronged despite its beauty. Head north up the coast, with overnight stops at Bandon [17] and Yachats [18] before heading over the Coast Range to Portland for a couple of nights of culture and fine dining before closing your travel diary.