Step into Portland’s wild past and uncover the stories that made this city famous for its eccentric spirit and rebellious heart. 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.

Between tales of mischief and mayhem, you’ll enjoy a stop for an iconic Voodoo Doughnut, a sweet taste of Portland’s weird side.

Your guide will lead you through hidden corners and historic landmarks, rooftop viewpoints, plazas steeped in history, and sites of scandal and mystery, all while sharing captivating stories of Portland’s colourful past and curious present.

Peak Tours is licensed and insured, local and family-owned, reliable and knowledgeable. We'd love to show you around!