Portland, Oregon, isn’t a city known for extremes. Our mild-mannered climate gently swings between cool summers and damp winters, our history is rich but lacks dramatic booms of wealth and industry, and our inhabitants are so easygoing that we actually stop our cars to let pedestrians cross the street.
Our architecture follows the same script. You won’t find boulevards peppered with gated estates of the super-rich here, or severely blighted areas of urban decay. We have no big-name architects’ masterworks, nor acres of bland, no-name development. What Portland does have—perhaps its greatest asset— is a living mosaic of inner-city neighborhoods filled with tens of thousands of charming and well-preserved early 20th-century homes.
Divided right up the middle by the Willamette River, Portland has an East/West split that defines more than the city’s geography and address system. On the Westside is the city’s urban center, which quickly rises into the 1,000′-high West Hills, where winding streets and forested canyons play host to view-blessed homes of the affluent. On the flatter Eastside, an endless grid spreads across a gently rolling landscape, where more modest middle- and working-class houses are woven into a patchwork quilt of neighborhoods both funky and elegant, sewn together by vibrant commercial streets, busy public schools, and beautiful city parks.
For the old-house explorer, Portland has treasures on both sides of the river, and seeing them will have a lot to do with how you plan to get around. The complicated and curving switchbacks of the West Hills can be a navigational challenge even for natives, and are more amenable to GPS-enabled automobile outings. The Eastside, on the other hand, offers a welcoming terrain that can be walked or biked with ease, and rewards adventurous wandering—so that’s where I recommend starting. From dozens of great neighborhoods on the Eastside, here are four of my favorites.
Platted in the late 1880s and recently named a National Register Historic District (Oregon’s largest), the 583-acre Irvington neighborhood is like a walk back in time. More than 90 percent of the 2,800 homes here were built between 1890 and 1950, and the vast majority still retain their original historic appearance. The state’s earliest use of restrictive development covenants resulted in a concentration of exceptional houses set well back on oversized lots in the heart of this lovely neighborhood. You’ll find perhaps the broadest range of house styles here, from Queen Annes and Colonial Revivals to Arts & Crafts and English Tudors. Many of Portland’s most talented early 20th-century architects built projects in Irvington, and dozens still survive.
Smaller, but perhaps better known, Ladd’s Addition was Portland’s first planned community and is also a National Historic District. In 1891, William S. Ladd subdivided a close-in 126-acre farm for a “modern” development with amenities like gas and electric lighting, paved streets, sidewalks, and a sewer system. Departing dramatically from the city’s strict orthogonal grid, his neighborhood was laid out in a distinctive L’Enfant-inspired radial street pattern, like a baseball diamond of four small public squares around a large central traffic circle.
With most of its homes built between 1905 and 1930, Ladd’s has a diverse mix of classic house styles, features formal rose gardens maintained by the community in the four squares, and is shaded by some of the tallest and most stately elms in the city. This neighborhood is one of the few in Portland with alleys, which makes for a fully rounded old-house gawking experience during which I can play my favorite game: “spot the closed-in sleeping porch.”
Between 1900 and 1930, partly fueled by exposure during the 1905 Lewis & Clark Exposition, Portland saw its population grow from 90,000 to 300,000—and those newcomers needed homes. Platted in 1909 from Hazel Fern Farm (another Ladd property), Laurelhurst was intended from the start to be a “high-class residence park” with some of the most restrictive building covenants ever enacted in the city. Only single-family homes were allowed, and these were required to meet minimum building costs.
The firm of Olmstead Brothers was hired to lay out the 400+ acres, and in yet another dramatic break from the city’s traditional planning, a series of concentric, radial, and gently curving streets were created that still consternate Portland’s grid-conditioned drivers today. While the same broad array of early 20th-century home styles can be found in Laurelhurst as other areas, this district has an especially nice concentration of fine Craftsman bungalows.
Alameda Ridge/Dolph Park
Alameda and Grant Park are adjacent neighborhoods with similar early roots in the 1910s. However, each of these areas contains a smaller district with a stellar collection of large, romantic Historic Revival-style houses built in the 1920s and ’30s. Alameda Ridge is the mini-West Hills of the Eastside, where fine (and expensive) homes meander along a prominent crest that offers stunning views over the city.
Within Grant Park, Dolph Park is like a trip to Disneyland for grown-ups, a tidy grid of remarkable Storybook “cottages” on immaculate lawns. Between the two, you’ll find some of Portland’s most substantial and imaginative Old English manses, Norman castles, and Mediterranean villas, sporting wrought iron balconies, stuccoed half-timber facades, faux-thatch rolled roofs, and massive chimneys of river rock and clinker brick.
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