Portland’s history is intertwined with the history of its illustrious and quirky mayors, from our second mayor who simply walked out of office to go gold digging and John Gates, who invented 72 different steamboats in his lifetime, to more recent mayors who have led the vanguard for ideas like cities as commutable hubs, incubators for small businesses and havens for artists.
This walking tour explores some of the downtown spots that remember and represent those various mayors over the city’s 150-year history. These mayors are responsible for what is, and what isn’t, part of Portland’s current state of being—its parks, its bike culture, and its defiance to conformity.
We’ll stop to talk about Henry Failing, who is responsible for the moniker “Stumptown”; Terry Shrunk, one of the longest-serving mayors who battled with Bobby Kennedy over gambling in Portland and is now honored with a downtown park; and Bud Clark, who famously exposed himself to art—and, in spite of his goofiness, was an earnest mayor who helped establish public art funding and bike culture in Portland.
The tour starts at downtown Voodoo Doughnuts, site of a midnight doughnut eating competition for mayoral hopefuls, and traces through the city’s inner westside, covering about two miles of terrain from Burnside to Portland’s current, century-old Italian villa-styled City Hall.
I'm Phil Busse, a member of the Atlas Obscura community.
Over the past 20 years, I have reported on and been part of local politics in Portland - with a certain focus on the city’s mayors and history. I helped launch the Portland Mercury, and was the publication’s Managing Editor, spending a good portion of my time at City Hall - so much so, that I ran for mayor in 2004, finishing third out of 26 candidates (behind a two-time city councilmember and the police chief, but in front of a clown and the naked guy on cable access television!).
Portland has a fascinating history that is told through its mayors—from the silly to the serious, the noble to the notorious, and including the sincere and scandalous in-between.
For questions about this experience, please contact me directly through Airbnb.
This event will run rain or shine.
There are 10 spots available on this experience.
Guests ages 8 and up can attend. Parents may also bring children under 2 years of age.
- Wear comfortable walking shoes.
- Bring a bottle of water and a snack.
Any experience can be canceled and fully refunded within 24 hours of purchase. See cancellation policy.