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Around Portland Tours

The Simpsons… The bike tour

9:30 a.m. departures, 3-4 hours, $75

Many bookings unavailable through mid July

Creator Matt Groening grew up in Portland; we call it “the REAL Springfield.” Our first-of-its-kind bike tour explores both the tangible evidence that Portland inspired The Simpsons (it’s carved into the very sidewalks and street signs), the almost-identical elementary schools and bullies, the skateboard culture. And then, see what the city took from the show. Could Portland’s donut craze have been created by the fictional Homer himself? We’ll make our case.

At the intersection of cartoon storytelling, history and culture, find the real truth behind The Simpsons.

Portland street names make many appearances in The Simpsons, beginning with Evergreen Terrace — the street creator Matt Groening grew up on. But the city boasts more than just the namesakes of many characters; it is the context in which the show was created, and the cultural manifestation of the show’s impact on American lives. 

Come along on a 11-mile bike ride that explores physical ties to the show, like the Bart Simpson drawing etched into the sidewalk near Groening’s high school, and the streets that give many characters their names. The ride also connects to the culture of the city as it has influenced, and been influenced by, the show. 

Visit the donut culture in the city, entirely developed during the show’s run, as well as the skateboard culture, which had its origins around the time the show began. Try a donut — and bring your skateboard into the halls.

Like no other tour, you will examine the great (and weird) true stories behind the origins of Krusty the Clown, Kwik-E-Mart, Krusty Burger, Jebediah Springfield and Manhattan Shelbyville, Moe’s Tavern, and Lisa’s flirtations with vegetarianism and Buddhism. 

Full of photo ops, fun facts, prank calls and of course donuts, this tour tells a story of a city and its most famous TV offspring… The Simpsons!

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