The Boys in the Boat by Daniel James Brown (2013) tells the story of the University of Washington rowing team that won gold at the 1936 Berlin Olympics. It is fundamentally a Depression-era Seattle book — the young men who make up the crew come from logging camps and fishing towns around Puget Sound — and Brown renders the city and the Pacific Northwest landscape with unusual care. It is also simply one of the best sports books written in recent years.
Snow Falling on Cedars by David Guterson (1994) is set on San Juan Island, a ferry ride north of Seattle, in the years after World War II. A Japanese-American fisherman is tried for murder, and the novel uses the trial to examine the internment of Japanese Americans during the war and its aftermath in the tight communities of the Pacific Northwest islands. The landscape and the maritime atmosphere are rendered with extraordinary precision.
The Tao of Pooh connection aside, the writer most associated with Seattle is the poet Richard Hugo (1923–1982), who grew up in White Center and taught for years at the University of Montana. His collection Making Certain It Goes On: The Collected Poems of Richard Hugo is the place to start — the poems set in Pacific Northwest mill towns and fishing villages capture a particular kind of mid-century American working-class landscape that has largely vanished. "Degrees of Gray in Philipsburg" is the most anthologised, but the Seattle poems are the most personal.
Emerald City by Peter Donahue (2009) is a novel set in 1990s Seattle through the perspective of various characters caught in the city's first wave of tech-driven transformation. It is accurate about the period and specific about neighbourhoods in a way that rewards visitors who know the streets.
Breaking Clean by Judy Blunt (2002) is set in Montana rather than Seattle but is the best book written about the culture of the rural Pacific Northwest interior — the ranching country east of the Cascades that is geographically close to Seattle and culturally a world away. Reading it before visiting the region gives context that a city-focused guide cannot provide.