About This Tour
Discover Portland's storied past on a walking tour that explores its scandals, legends, and quirks. The perfect tour for those who like history with a wink, a shiver, and a dash of unexpected! This walking tour begins in Old Town, where we pull up the cobblestones to reveal the ghosts of rough-and-tumble early Portland. Once a lawless frontier outpost, the city was rife with scandal, from the infamous Shanghai Tunnels and floating bordellos to political intrigue and legends that grew as tall as the trees. Along the way, you’ll learn why Portland earned the nickname “Little Beirut,” how an Oregon governor once funded a rock festival, and how the city’s Naked Bike Ride became an unexpected symbol of protest and peace. We'll enjoy a stop for an iconic Voodoo Doughnut, a sweet taste of Portland’s weird side. Peak Tours is licensed and insured, local and family-owned, reliable and knowledgeable. We'd love to show you around!
Photo Gallery
The Original Sweet Sin Voodoo Doughnut: Where “Keep Portland Weird” became a sugar-coated mission.
The Icon Herself, Darcelle XV: The legendary performer who turned Portland into a beacon of bold self-expression.
Secrets Beneath the Bridges: Tour guests explore the shadows where Portland’s strangest stories took shape.
Queens of Old Town: A dazzling drag queen keeping the legacy of glitter and rebellion alive.
Union Station Storytime: A tour group at the iconic station where countless scandalous journeys began.
We'll discuss the West Coast’s wildest watering hole, where fortunes (and morals) slipped away.
Tour Analysis
Tour Characteristics
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What's Included
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Additional Information
Meeting Point
Feel free to wait inside the cafe. Your tour guide will arrive 5-10 minutes before departure.
Cancellation Policy
All sales are final. No refund is available for cancellations.
✓ Free cancellation due to bad weather
Tour Operator
Peak Tours and Transit
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Book Weird and Wicked: A Portland Walking Tour for the Scandal-Curious
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