Portland’s Coolest Walking Tours

Image: Holly Andres
Know Your City’s walking tours are a little…different. To wit:
Richard Berry’s 1955 single, “Louie, Louie”, was the subject of a full criminal investigation after the FBI received an outraged letter outlining the crude sexual expletives the writer thought he could hear in the tune (the FBI later confirmed it was actually the chaste tale of a Jamaican sailor returning home). Meanwhile, white singers recorded covers of the song to great public acclaim—the most popular version was the 1963 hit by Portland band the Kingsmen.
Know Your City covers this and other historical nuggets in its “Sing a Song of Portland” tour, led by a troubadour guide and featuring group sing-alongs as participants learn about various musical landmarks in the city. “We talk about how musical culture can reveal social justice issues of the time,” says KYC’s programs coordinator Amanda Tillstrom.
Another new tour, “A People’s Guide to Portland,” will focus on the experiences and contributions of historically marginalized communities in Portland, especially in the wake of modern gentrification. “We talk about how Portland is known as an extremely white and gentrified city,” says Tillstrom. “And we discuss how different communities are affected by that today and how they have historically been affected.”
Know Your City began as the Dill Pickle Club in 2009, at its core a “loose group of friends interested in leading adult field trips and learning about Portland,” according to Tillstrom. Today, Executive Director Marc Moscato is the only remaining founder, but the original spirit of the nonprofit is still vibrant.
“Our overall goal is to engage people with where they live through place-making practices,” says Tillstrom. The organization approaches this task from several directions, including a robust youth program that has yielded gems like a comic book class with a civil rights focus, and the Jade Journal program, a multilingual newspaper composed by fifth-grade students at Harrison Park Elementary School and released this February. “We talked to kids about what it’s like to live in Portland, and how it’s so much more than simple geography,” says Tillstrom. “They put together this amazing newspaper talking about topics from equity to food deserts to ‘is the internet making us stupid?’”
Walking tours depart from KYC’s bike kiosk in Old Town’s Ankeny Alley, and are free with a suggested donation for the guides. Check out the Know Your City website for more information.