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Oregon is easily divided up into thirds: the Oregon coast to the west, the Williamette Valley and Cascade Mountains a bit to the left of center, and desert plateau to the east. Oregon’s main hub (and a destination that deserves to be on your itinerary) is Portland, a city that sits to the high north of the Williamette Valley, hovering just below the Oregon/Washington boarder.

Oregon Cities and Regions

Willamette Valley

Thanks to its temperate climate and flat terrain, grapes thrive in fertile Willamette Valley, also known as Oregon’s wine country. Over 200 wineries (most of which are concentrated between the towns of McMinnville, Yamhill, and Newberg) take advantage of the rich soil to produce pinot noirs, pinot grigios, chardonnays, and Rieslings. Just east of the coast, this stretch of land includes Oregon’s largest cities – Portland, Eugene, and Salem.


Located just below the Washington state line on I-5, Portland, the largest city in Oregon with a population of just over half a million, is the epicenter of Generation Y – hip, bohemian, and greener-than-green. The city is a gorgeous architectural conglomeration of Victorian buildings with their arched windows, glazed terra-cotta exteriors and modern glass-and-steel creations. The Williamette and Columbia Rivers cut through the city, criss-crossed by a multitude of picturesque bridges. Also known as “Rose City,” due to the abundance of rose gardens here, Portland weaves together lush public parks, museums, music venues, and the world’s largest new and used bookstore (Powell’s). This is one of the last places you’ll ever need a car: your feet or a public bus, light rail, or streetcar can get you just about anywhere. Bicyclers are everywhere. See our Portland Travel Guide


Eugene has the kind of charm that only college towns have, thanks to the University of Oregon. Smack dab in the middle of western Oregon, this city, the third largest in Oregon, is a must stop on I-5. The downtown district retains a small town, bohemian ‘60s feel with live folk music and street performers on the weekends. The centrally located Lane County Fairgrounds frequently hosts games, fairs, concerts, and a very popular summer carnival in July. Fans of the cult film Animal House will be interested to know that the movie was filmed here in 1977.


Forty-seven miles to the south of Portland you’ll find Oregon’s capitol and second largest city after Portland. The focal point of the city is the stunning Capitol Building, destroyed twice by fire and built in its current incarnation in 1938. Enormous “wings” were added to the building in 1977 and today the white Modern Greek structure sprawls across several blocks. Unless you care a great deal about architecture or are visiting family nearby, however, Salem is one of those towns that you can skip without feeling guilty.

Oregon Cascades: Mt. Hood, The Gorge, and Crater Lake National Park

The Oregon Cascades cover over 700 miles and reach from Oregon’s tallest mountain (Mt. Hood at 11,249 feet) in the north, all the way down to North America’s deepest lake (Crater Lake, at a depth of 1,943 feet) in the south. This region includes the awe-inspiring Columbia River Gorge which forms the border between Oregon and Washington and stretches for 80 miles. The Cascades are prime skiing territory and provide a great number of superb backcountry recreation opportunities. The best way to access the Cascades is to take Highway 26 from Portland until you reach Mount Hood and the Madras. From there, take US-97 south into the Cascades.

Oregon Coast

Drive the length of Oregon’s 363 miles of Pacific coastline. The 8 hour trip is worth it for the dramatic scenery, which ranges from rugged cliffs to sandy dunes, and includes quaint towns and picturesque lighthouses along the way. Popular stops include Coos Bay to the south (the largest city on the coast and Oregon’s main seaport) and Cannon Beach to the north, known for its local art scene and scenic strands.

Central Oregon

At its heart, Oregon is a land of high desert county smattered with a few mountain peaks. Sunshine and moderate year-round temperatures make this area and outdoorsmen’s dream. Hiking, fly-fishing, golfing, and rock-climbing are popular; in the winter, fresh snow in the mountains spells skiing and snowboarding opportunities.

Southern Oregon

Visitors travel to southern Oregon for the diverse wilderness. Amongst the endless Douglas firs and switchback side roads, spelunkers can explore the depths of a marble cave at the Oregon Caves National Monument and avid hikers can traverse the rim of Crater Lake. Grants Pass is a great entry point into the Rouge River for those in search of whitewater rapids. Fishing, canoeing, and bird-watching are top-notch in Klamath Basin National Wildlife Refuges. Southern Oregon also has the 50 preserved covered bridges – the largest number in the West.

Eastern Oregon

Desert lands, snow-capped mountains, and wild rivers blanket the Eastern edge of Oregon. Follow the Snake River down Oregon’s eastern border and see why this natural wonder was a formidable one on the Oregon trail. Let your jaw drop at the Technicolor Painted Hills (part of John Day Fossil Beds National Monument), hike the Steens Mountains for fantastic desert panoramas, and visit Hells Canyon, which at 7,913 feet (that’s 1,000 feet deeper than the Grand Canyon), is the deepest river gorge on the North American continent.

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