Reading Portland presents a complex overview of Portland's progress from the time of its establishment to the modern day, compiled from the writings of over 80 authors whose genres range from fiction to memoir. While many outstanding writers are featured in the collection—including Rudyard Kipling, Northwest darling Beverly Cleary, and famed Fight Club author Chuck Palahniuk—it is the authors' diversity of sentiment, style, and time period which creates an interesting and varied perspective of Portland, and ultimately gives the reader great insight into the city's history.

Featured in the collection are several works that criticize the development of the city. In an excerpt from Kipling's 1906 From Sea to Sea: Letters of Travel, the author browbeats Portland for being "so busy that it can't attend to its own sewage or paving." Similarly, in his 1884 Memorie and Rime, Joaquin Miller (the so-called "Byron of Oregon") discusses the unfortunate disappearance of Native Americans in the region, and calls the new Pacific Railroad, "a sort of siphon, which let in a stream of weak and worthless people."

While Kipling and Miller's work explores the failures within the city's progress, authors John Reed and Cleary provide personal accounts of life in the city. Reed's 1936 article, "Almost Thirty," chronicles his middle-class upbringing in Portland, peppered with descriptions of "slummy" Goose Hollow and Chinese servants; Cleary's 1988 A Girl from Yamhill: A Memoir, similarly references Portland landmarks.

To round out the collection, an excerpt from writer Ursula K. Le Guin's 1971 The Lathe of Heaven—set in a futuristic, overpopulated Portland—adds a sci-fi element, and Palahniuk's 2003 Fugitives and Refugees: A Walk in Portland, Oregon offers profiles of Portland locals.

While some of the selections may seem like odd additions to a collection meant to celebrate Portland, editors John Trombold and Peter Donahue should be commended for presenting such honest and varied first-hand accounts of the city, from the perspective of both natives and outsiders alike.