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The Oregon Trail

Coming in from the west on the Sunset Highway (US-26), our route enters Portland next to the Sylvan-Highlands neighborhood’s Washington Park, then crosses the downtown area along Jefferson and Columbia Streets. Crossing the Willamette River, US-26 follows Powell Boulevard across East Portland.

Portland, Oregon’s largest city, is located inland from the coast near the confluence of the Willamette and Columbia Rivers. Due to its strategic location, the pioneer municipality grew so fast it was nicknamed Stumptown for the hundreds of fir stumps left by early loggers. While railroad tracks and other heavy industrial remnants are still visible around town, Portland’s riverfront park and numerous winding greenways show that this mini-metropolis is a community that values art and nature as highly as commerce. Along with one of the largest (5,157-acre Forest Park) and the smallest (452-square-inch Mill Ends Park) urban parks in the nation, and one of the coolest urban skate parks anywhere (under the Burnside Bridge), Portland also has more movie theaters and restaurants per capita than any other U.S. city. It ranks high in microbreweries and bookstores per capita as well.

In the lively Old Town district, cast-iron facades of 120-year-old buildings hold some of the city’s most popular bars, clubs, and cafés. South of Old Town along the river, an ugly freeway has been torn down to form the Governor Tom McCall Waterfront Park, and west of the river, downtown Portland centers on lively Pioneer Courthouse Square, at 6th Avenue and Yamhill Street. South of the square, the South Park Blocks between Park and 9th Avenues were set aside as parklands in 1852 and are now bounded by Portland’s prime museums. One essential Portland place is north of the square: Powell’s City of Books (1005 W. Burnside St., 800/878-7323) is the largest (and certainly among the best) new-and-used bookshop in the world.

One of the largest and oldest ballparks in the minor leagues, the 1926 Providence Park, a half mile west of downtown, saw one of the first outdoor rock concerts when Elvis Presley played here in 1957, and was home to the Portland Beavers ball club until 2010, when baseball was booted out to make room for Portland’s pro soccer team, the Timbers.

Along the river 6.5 miles south of town is the wonderful circa-1905 Oaks Amusement Park (503/233-5777), with ancient and modern thrill rides and a roller-skating rink, all packed together in a sylvan oak tree-dotted park.


Air travelers can land at Portland International Airport (PDX), but most long-distance flights come and go via Seattle’s Sea-Tac, which is only about a three-hour drive north, via the I-5 freeway. Getting around public-spirited Portland is a breeze thanks to the efficient bus and light rail train system (503/238-7433, from $2.50).

Portland has great places to eat and drink, in all stripes and sizes. Screen Door (2337 E. Burnside St., 503/542-0880) draws lines for its locally sourced organic versions of Deep South faves like fried chicken, shrimp ’n’ grits, BBQ brisket, and apple rhubarb pies. Nothing beats the RingSide Steakhouse (2165 W. Burnside St., 503/223-1513), 1.5 miles west of downtown, famous for its beef, fried chicken, monster Walla Walla sweet onion rings, and Hemingway-esque ambience. For over a century, Jake’s Famous Crawfish (401 SW 12th Ave., 503/226-1419) has been the place to go for the freshest seafood. If your taste happens to run more to Marilyn Manson than Marilyn Monroe, you’ll prefer to eat across town at Dot’s Café (2521 SE Clinton St., 503/235-0203), a late-night hangout that has comfy dark booths, great black-bean burrito bowls, brews, and a pool table. One last must-eat is Voodoo Doughnut (22 SW 3rd Ave., 503/241-4704); the original location is packed during Old Town Portland’s popular Saturday Market but worth a visit any other time (it’s open 24 hours).

There are all sorts of places to stay in Portland, starting with a pair of popular HI-Portland Hostels, one east of downtown (3031 SE Hawthorne Blvd., 503/236-3380) and another in the Northwest District (427 NW 18th Ave., 503/241-2783). Hotel deLuxe (729 SW 15th Ave., 503/219-2094, $135 and up) is stylish, comfortable, and close to downtown. For a splurge, try The Heathman Hotel (1001 SW Broadway, 503/241-4100 or 855/516-1090, $209 and up), an impeccably restored downtown landmark, with an elegant lobby and sumptuously appointed (if somewhat small) rooms.

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