Portland is a young city. It was incorporated in 1851, which makes it far younger than most urban areas on the East Coast, much less Europe or Asia—but it still has history. Even over the course of a mere 175 years, the city has reshaped itself again and again, and almost every city block has a story behind it.
In Search of Portland, the new book by local journalist and architecture writer Brian Libby, explores those stories and locations, revealing layers of history buried under present-day architecture.
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Libby structures the book as a series of walks through Portland’s west side, and his narration reads like a knowledgeable tour guide sharing anecdotes, trivia, and fun stories associated with places of note. This includes marquee sites like the Portland Building and City Hall, but also Libby’s very first apartment building, an unassuming brick structure downtown.
Each profile is long enough to feel like it goes deep, but short enough to be interesting. Locations also serve as springboards to explore other topics related to Portland’s history. A description of an apartment complex turns into two different digressions: One about departed local author Ursula K. Le Guin and the other about the 1977 Portland Trail Blazers. Stories, sometimes unrelated, jump out of locations.
But Libby makes this occasionally disjointed structure work. His first-person narrative feels like you’re taking a walk with a friend who knows a ton of Portland trivia, and is compelled to tell you everything he knows about a given building, block, or landmark.
Like strolling along with a good tour guide, the anecdotes within In Search of Portland are short, full of detail, and make you want to read the next one. That’s by design.
“When you’re on a real walking tour you have to limit yourself,” says Libby. “As a tour guide, you might have an hour’s worth of material, but as soon as you get to about three minutes, people start to get antsy and want to move on.”

In Search of Portland does have one big, glaring issue. It only talks about the west side. While downtown and Old Town certainly have a lot of history, most of Portland’s neighborhoods are on the opposite side of the Willamette River. However, if the book did go into detail on all six of Portland’s quadrants, it would be enormous.
“Early on, I wrote a whole chapter that took place in Southeast. It wasn’t intuitive that I was only going to walk through the downtown corridor, Old Town, and the Pearl,” says Libby. “There was an early draft of the book that was way, way too long.” Still, the absence of the east side is palpable.
In Search of Portland is about a changing, built environment. Each entry tells of construction, demolition, renovation, repurposing, new owners, businesses opening and closing, and how nothing ever really stays the same. Almost fittingly, Portland’s history has already lapped the book, making one of its entries out-of-date even before it hit the shelves. Centennial Mills features prominently in Libby’s second chapter and has been mostly demolished as of this writing.
“It seemed obvious that the rest of Centennial Mills was going to go at some point,” says Libby. “The city of Portland has been engaging in what I call ‘demolition by neglect’…. They never had the gumption to tear it down, because they know people love it. But they have continually declined to give it any kind of funding, either to renovate it as a building, or stabilize it as a ruin and build a park around it. I was really sad when Centennial Mills caught fire, but it seemed inevitable.”
Despite the fate of Centennial Mills, Libby maintains that Portland has a “decent record with historic preservation.” Portland, he says, is much more likely to renovate or improve existing structures than build wholly new projects.
For Libby, though, the book is about the passage of time, and he acknowledges that buildings falling into disrepair or meeting their ends, whether because of fires or wrecking balls, is par for the course when you write about historic architecture. This is especially true, he says, with the possibility of a large earthquake in the future. The prospect of potentially losing several buildings throughout the city, especially old brick structures, was a big motivator for Libby to document what’s still standing.
Every building dies eventually. Some get reborn via renovation or rebuilding. When that happens, they leave behind a new layer of history.
Brian Libby discusses In Search of Portland with art critic Richard Speer at Powell’s City of Books, 1005 W Burnside, Tues Sept 15, 7 pm, FREE, powells.com, all ages. Libby also hosts In Search of Portland: Short Films From the 1930s at PAM Cut’s Tomorrow Theater, 3530 SE Division, Thurs Oct 8, 7 pm, $15, more info at tomorrowtheater.org.
