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...
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.
Don't miss these unforgettable moments
- Why Holley thought of himself as a teenage "brown-skinned Kerouac" in Michigan
- Walking barefoot on an Oregon beach with a wealthy stranger in a red convertible
- The mom who's single-handedly saving her town's crumbling teen center with mop buckets and determination
- A white-knuckle ride with a speeding driver on his way to DUI court
- The paper mill ghost town and one man's 15-year story of economic change
- Sleeping on a church roof under the stars (and why Holley calls it "urban camping")
- The Willie Nelson cassette tape that sparked a conversation about human connection
- How three days on Highway 101 revealed Holley's future as a journalist
Resources
- Visit Santi Elijah Holley's website: santielijahholley.com
- Read his book An Amerikan Family: The Shakurs and the Nation They Created
- Read the transcript of the episode
- Read Santi's Afar story about New Orleans
Be sure to subscribe to the show and to sign up for our podcast newsletter, Behind the Mic, where we share upcoming news and behind-the-scenes details of each episode. And explore our other podcasts, Unpacked, which unpacks a tricky topic in travel each week, and View From Afar, where we spotlight the people and the ideas shaping the future of travel.
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