For nineteenth-century pioneers on the arduous Oregon Trail, the rich and fertile Willamette Valley was the promised land of Oregon (OR-uh-gun), and it’s still the heart of the state’s social, political and cultural life. Portland, the biggest city, is centralized and walkable, with a cosy European feel; Salem, the state capital, maintains a small-town air; and Eugene is a likeable college community.

East of Portland, waterfalls cascade down mossy cliffs along the beautiful Columbia River Gorge, south of which looms the imposing silhouette of Mount Hood. Central Oregon is based around the popular recreation hub of Bend, while further south around Grants Pass, the major rivers carve steep gorges and make for some excellent whitewater rafting, and the liberal hamlet of Ashland offers a splash of culture with its annual Shakespeare Festival.

The Oregon Coast’s most northerly town, Astoria, enjoys a magnificent setting strewn with imposing Victorian homes, while farther south, wide expanses of pristine sand are broken by jagged black monoliths, and pale lighthouses look out from stark headlands over sheltered coves. Finally, the rugged deserts and lava fields of Eastern Oregon are much more remote, and some small towns still celebrate their cowboy roots with annual rodeos.

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  • Portland
  • Bend
  • Hells Canyon
  • The Oregon Trail