When Santi Elijah Holley, writer and author of An Amerikan Family: The Shakurs and the Nation They Created, was 25, he took the ultimate travel leap of faith: He hitchhiked 400 miles from Northern California to Portland through small-town Oregon. But for Holley—who had just moved to Portland from Michigan—it wasn't just about getting a ride. After a year of feeling like an outsider as a person of color in one of America's whitest states, this journey would test whether Oregon would accept him or leave him standing on the side of the road.

What he discovered during those three days hitchhiking along Highway 101 changed everything. From sleeping on church roofs to walking barefoot on the beach with a wealthy New Yorker, and listening to a mother's fight for youth spaces to riding with speeders heading to court, Holley found that Oregon's people had stories to tell—and that he was the perfect stranger to hear them.

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