Oregon Travel Guide

For nineteenth-century pioneers on the arduous Oregon Trail, the rich and fertile Willamette Valley was the promised land of OREGON, and it’s still the heart of the state’s social, political and cultural life. Portland, the biggest city, is alternative, creative and one of the coolest cities in the USA right now; Salem, the state capital, maintains a small-town air; and Eugene is a lively, outdoorsy 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 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.

Ashland and the Shakespeare Festival

The progressive hamlet of ASHLAND, 180 miles south of Eugene, is the unlikely home of one of the world’s best tributes to Shakespeare, the Oregon Shakespeare Festival, actually a repertory theatre company, founded in 1935. Its season runs from February to early November, offering eleven different plays; four by Shakespeare and seven by other classic, modern and contemporary writers. Performances take place in the half-timbered Elizabethan Theatre (early June to mid-Oct) and adjacent to it, the Angus Bowmer Theatre, which stages both classical and more recent works, and the austere Thomas Theatre, which has a mostly modern repertoire. The three theatres share the same box office, 15 S Pioneer St (osfashland.org).

If you come in the summer, head twenty miles northwest to the preserved Old West hamlet of Jacksonville for the annual Britt Festival (June–Aug; brittfest.org), to hear the top names in jazz, pop, rock and country music.

The Columbia River Gorge and Mount Hood

East of Portland the Columbia River Gorge cuts through the snowy peaks of the Cascades for 75 miles, an important corridor between east and west for thousands of years. Scoured into a wide U-shape by huge Ice Age-era floods, the gorge is a nationally protected scenic area (fs.usda.gov/crgnsa), where waterfalls tumble down sheer cliffs, and fir and maple trees turn fabulous shades of gold and red in the autumn.

Dominating the horizon south of the Columbia River and the town of Hood River, Mount Hood (11,240ft) is a mesmerizing dormant volcano and the tallest peak in Oregon, sprinkled with eleven active glaciers. The Mount Hood Scenic Loop – a combination of highways 35 and 26 – links the mountain and the Columbia Gorge while passing numerous orchards along the way, which in the spring and summer offer great opportunities to sample fresh fruit, juice and desserts (see hoodriverfruitloop.com). One of the other joys of the area is to explore the mountain via trails radiating out from its slopes, most of them protected within the Mount Hood National Forest; ranger centres can supply more information. Note that there are no trails to the summit of Mount Hood; only experienced mountaineers should tackle the technical climb to the top (free permits required).

Near the intersection of highways 35 and 26, a turnoff leads to the grand, New Deal-era Timberline Lodge, which Stephen King fans might recognize as the exterior set for the hotel in Stanley Kubrick’s The Shining.

Crater Lake National Park

Just over a hundred miles south of Bend, the blown-out shell of Mount Mazama holds the hypnotically beautiful CRATER LAKE, formed after an explosion 42 times greater than that of Mount St Helens. You won’t forget the first time you peer over the volcano rim: the biggest island on the lake, Wizard Island, is actually the tip of a still-rising cinder cone, and the so-called Phantom Ship is a jagged volcanic dyke that, in dim light or fog, resembles a mysterious clipper on the water. In its snowy isolation, the lake, at a depth of nearly 2000ft, is awe-inspiring; in summer, wild flowers bloom along its high rim.

Regular boats cruise the lake, reached via the sheer, mile-long Cleetwood Cove trail (June–Oct) which provides the only access to the lake surface (700ft down). The trail is on the north edge, but visitor facilities are clustered on the south edge at tiny Rim Village. Other activities include scuba diving (June–Sept; free permits) into the depths of the deep, blue lake.

The Oregon Country Fair

Ten miles west of Eugene on US-126, little Veneta hosts the Oregon Country Fair (oregoncountryfair.org) in July, a long-standing hippie festival of music, art, food and dancing. Traffic can be heavy, and even if you have a car it’s easier to go by bus – the LTD has special services.


Long overshadowed by West Coast hot spots San Francisco and Seattle, eco-friendly, organic PORTLAND is increasingly matching its rivals in the hipster cool stakes, with booming arts, culinary, coffee and microbrew scenes, an inexplicably large number of indie cinemas serving beer and an alternative, outdoorsy culture lampooned in cult US TV show Portlandia. Celebrated local writer Chuck Palahniuk, who started his career here, describes the city in his travelog Fugitives and Refugees; while there are no major show-stoppers, its eccentric characters, cafés and markets, leafy parks and eclectic neighbourhoods make it the most enticing destination in the state. The city is famous for its bicycling culture, and visit in June and you’ll see why it’s also known as the “City of Roses”, with public gardens overflowing with blooms. The Willamette (pronounced “wuh-LAM-it”) River bisects Portland into its east and west sides, with the downtown core between the river’s west bank and the I-405 freeway, but to really get to grips with the city you’ll need to sample the neighbourhoods.

The city was actually named after Portland, Maine, following a coin toss between its two East Coast founders in 1845 (“Boston” was the other option). Today Portland is booming, with the likes of Nike and Columbia Sportswear based here, Intel a major employer and Adidas making the city its North American headquarters. That’s not to say things are perfect; as you’ll soon realize, Portland has a major homeless problem, with some estimates claiming up to two thousand minors on the streets at any one time.

Riding and surfing the dunes

The Oregon dunes are famous for their OHV (off-highway vehicle) opportunities, with special areas set aside for all manner of thrills and spills (get maps from the visitor centre). Various sand buggies, ATVs and dirt bikes can be rented at San Dunes Frontier, four miles south of Florence on US-101 (March–Sept; sanddunesfrontier.com), while the art of sandboarding (surfing on the dunes) can be mastered at Sand Master Park, 5351 US-101 in Florence (sandmasterpark.com).

Sea Lion Caves

Some 38 miles south of Newport, US-101 passes the extraordinary Sea Lion Caves (sealioncaves.com), America’s largest sea cave system and often crammed with hundreds of lounging, barking sea lions – you’ll smell them before you see them. The caves are accessed via a 225ft elevator; you’re most likely to see sea lions in autumn and winter (they are often perched on the rocks outside in summer).

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Andy Turner

written by
Andy Turner

updated 26.04.2021

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