Arguably the most important cultural export from Portland in the last 35 years, The Simpsons is known internationally as one of the most incisive sources of satire for American culture. What many people don’t know, is that the acclaimed animated series got its start right here in Portland. That’s right, Matt Groening, the creator of the series was born and raised on the West side of town. 

Long-time viewers of the series know that it is a running joke that the exact location of Springfield, the fictional home of the Simpsons, is never fully revealed or confirmed. In fact, many times the writers have gone out of their way to make it impossible to be anywhere in the US, while still being an American town. This creates a generic vision of Springfield as it represents all of America, and all that comes with it. In a way, Portland does represent America. It’s a proper city, while not being a mega metropolis. It also struggles with many of the issues facing Americans these days including housing, gentrification, sprawl, drugs, and density.

Historically, our city has more links to other American cultures like New England and the Midwest in contrast to Seattle and San Francisco which have more links to international cultures and capital. And while Portland is fairly progressive in its politics, but like Woody Guthrie said is “50 years behind Seattle in radical temper.” Portland can be thought of as a microcosm of America, and Springfield -loosely based on Portland- then becomes a place perfect for satire that can be related to by most Americans. 

 Here we’ve compiled a list of all the Simpson characters and local streets/landmarks that inspired them:

Northwest Portland (where the alphabet makes it easy)-

NW Flanders Street (also in NE)- Ned Flanders, the devout and obnoxious neighbor.

NW Kearney Street- Kearney Zzyzwicz, one of Bart’s bully frienemies.

NW Lovejoy Street- Reverend Timothy Lovejoy, the Presbylutheran minister. Of course.

NW Quimby Street- Mayor Joe Quimby, a loose parody of John F kennedy.

Southwest Portland:

SW Terwilliger Boulevard- Sideshow Bob Terwilliger, Bart’s nemesis.

North Portland- 

N Van Houten Avenue- Milhouse Van Houten is Bart’s best friend.

Grab bag- 

Montgomery Burns is named after Burnside Street and Montgomery Park, a well-known landmark building in Northwest Portland.

The Simpsons Itinerary

To make it the ultimate Simpsons days, grab your green skateboard and follow this itinerary on your way back to your couch, just in time for the show. 

Start out on (Millhouse) Van Houten Ave. near the campus at the University of Portland, one of the oldest schools in the state, and home to one of the best collegiate women’s soccer teams in the world. Walk along local secret Willamette Boulevard, with rare views southward of the city center. Head West to the striking and elusive turquoise St. John’s Bridge, which very few visitors to Portland get the chance to see. On the way, you may spend some time in St. John’s, which was its own town until 1915. It has a cute little town center area, and the famous statue of Paul Bunyan with his red and white checkered shirt and big axe.

Once across, you will be on the West side of the river, and East side of legendary Forest Park. Here, it is your option if you wanted to continue the walk down highway 30, but I would recommend heading up from there into Forest Park and taking our world-class urban trail system. For more on hikes in Portland, check out our previous post on places to hike within the city.

Whether you find yourself on industrial Nicolai St. in NW or come out at the base of beautiful lower MacLeay Park, you will just be a few blocks from Montgomery Park, the former Montgomery Ward building and namesake of Montgomery Burns. Now the building is used to trade shows after the steady 20th-century decline of large-scale department stores. 

Montgomery Park is looking out over Vaughn and Wilson Streets, so you can head south up the alphabet through Quimby, Lovejoy, Kearney, and Flanders Streets on the way to Burnside, the other namesake of everyone’s favorite evil billionaire. Depending on how far west you went from Montgomery park, you could find yourself either in the Nob Hill neighborhood or Pearl District. A stroll down 23rd, 21st, or 13th Avenues in particular are popular shopping and sightseeing routes. Once at Burnside, you might as well visit our world-class bookstore, Powell’s Books between 10th and 11th. Heading South from there along 9th will eventually lead to the South Park Blocks and through the campus at Portland State University-  with its beautifully integrated urban campus. 

Make your way to Broadway, and keep heading south until you go over interstate 405. Then head down towards 6th until heading up past Duniway Track up the hill, following signs to OHSU. 6th will Quickly turn into Terwilliger Boulevard, which goes up into the West Hills

A detailed route is laid here on Google maps 

(Photo credit https://www.photosforclass.com/search/the%20simpsons)