Last Exit to Springfield: How America’s coolest city made The Simpsons

by Mike MacEacheran Jul 17, 2023 4 minutes

Hi-diddly-ho! I was enjoying a morning tour through the Alphabet District of Nob Hill in Northwest Portland, and I felt as though I was being stalked by a cast of goofy cartoon characters. The neighbourhood is all close-knit Colonial Revival houses, coffee shops, and burger and beer taverns where you could easily find yourself trapped for hours – and yet there is something else at work here.

First, we walked past a sign for Quimby Street. Then, in quick succession, we crossed Lovejoy Street, Kearney Street and Flanders Street. To the south of the neighbourhood, I was told there is a Burnside. I also learnt about Montgomery Park and Van Houten Avenue. I’m no map geek, but I am, I confess, a super fan of The Simpsons – and I found myself drawn into the story of its origin in Portland like Homer to Duff Beer.

“Portland’s not Springfield where the cartoon is set, that’d be too contrived,” said guide John Moran, of America’s Hub World Tours, as he recounted the backstory of America’s longest-running scripted primetime show (after first appearing on The Tracey Ullman Show in 1987, it’s now up to 34 seasons and counting).

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“There are no Simpsons museums or themed attractions here, but if you know where to look it’s pretty obvious Portland’s in the show’s DNA.”

Portland shares plenty of street names with Simpsons characters – and is that Mount Springfield in the background? (Getty Images/iStockphoto)

Certainly, these days, there is a throng of destinations allied to TV shows, and set-jetting on ‘location vacations’ is a bankable travel trend. HBO has made stars of the swanky hotels, villas and restaurants used in Succession, while Albuquerque, New Mexico, is now synonymous with Breaking Bad, as is Baltimore, Maryland, with The Wire and Snoqualmie, Washington, as the home of Twin Peaks. Not to mention the extra star-power sprayed all over Hawaii, Sicily and reportedly Thailand with each new series of White Lotus. Cartoons are another matter entirely, of course; and yet, if a TV show is the sum of its creator’s influences, The Simpsons is steeped in the spirit of Matt Groening’s Portland.

By that measure, the most important address in the city is 742 Evergreen Terrace, where The Simpsons’ cartoonist grew up in the 1950s – with father Homer, mother Marge and younger sisters Lisa and Maggie, all of whom Groening named his most famous characters after. His childhood home is hidden at the end of a long suburban road that switchbacks through the redwoods of Washington Park, as if to keep the house a secret (fans of the show will know the Simpsons family also live at the same address in the cartoon).

The park itself, with party piece rose gardens and beehive hairdo shrubbery, is a museum of living trees, where hiking trails unlock views of Downtown Portland and the meandering Willamette River. Miles away still is the arrowhead cone of Mt Hood, a forest-ringed stratovolcano that has an uncanny likeness to the cartoon’s totemic Mount Springfield.

Below Washington Park, our next stop wouldn’t make it onto many visitor itineraries. It is a no-frills bicycle and pedestrian bridge over an interstate that first opened two years ago. But it is also one that has been re-dedicated to honour Homer Simpson’s do-gooder next-door neighbour and nemesis, who, as it happens, was named after one of Portland’s founding fathers.

The character of Ned Flanders has been immortalised on a bridge over an interstate (Mike MacEacheran)

Part of me finds the Ned Flanders’ Crossing a bit silly, but the fan boy inside applauds the nonsense. If you come 10 years from now, there’ll probably be a shrine dubbed with all manner of “okily-dokily” catchphrases (a personal favourite: “Can I make my famous mimosa? A little sparkling water in a glass full of regular water?”).

Just as important, the overpass acts as a transition from Northwest Portland and Lincoln High School (Matt Groening’s alma mater; there was never a Principal Skinner, though) to the arty Pearl District and Old Town, where most out-of-towners come to sample doughnuts Homer would sell his soul for. Voodoo Doughnut, opened 20 years ago, with its novelty designs and ingenious toppings, is as nutty as Portland gets. The classics are a voodoo doll, with raspberry jelly and staked with a pretzel, a bacon maple bar, and a creative take on male genitalia filled with Bavarian cream.

It’s little coincidence, perhaps, that America’s self-styled capital of doughnuts and beer – the city has more than 70 inner-city breweries, after all – had a clear influence on forming Homer’s addictive personality. Simpsons fan or not, you’ll likely know the much-quoted line: “Here’s to alcohol: the cause of, and solution to, all of life’s problems.”

In the same neighbourhood at weekends, the riverfront also welcomes the largest arts and crafts market in the US. Pen and ink artworks and giclée paper prints are always front and centre, daubed in bright sunflower yellow, sky blue and bubblegum pink.

Like the fictional Springfield, Portland has a statue at the centre of town (Getty Images)

Portland’s living room is Pioneer Courthouse Square, and it’s a different setting today to the one Matt Groening experienced before he moved to Evergreen State College in Olympia, Washington, to hone his love for animation. There is still plenty of deep-rooted Oregonian history here, but a visit to Downtown and the close by Willamette riverfront needs to be tempered by an acceptance of the city’s current homeless epidemic, which has seen tent encampments surge and the numbers of unhoused Portlanders spiral. For the time being, City Hall’s motivation to fix the problem somewhat moderates the tension between the haves and have-nots.

All this is juxtaposed with the grandeur of Portlandia – a monstrous copper repoussé monument, second only to the Statue of Liberty in size – as well as Portland’s dozen steel and deck arc bridges scattered along the riverfront. These lead out across the city to the former site of the Trojan Nuclear Power Plant (an obvious reference point for Mr Burns’ operation); to the genuine city of Springfield in Central Oregon; to Eugene, where Matt Groening was inspired after a visit to a Moe’s-style tavern; to Seattle, the clear inspiration for fan favourite episode Marge vs. the Monorail; and, ultimately, all the way to Los Angeles, where the story of The Simpsons continues unabated today.

“Matt Groening set out to create a place that satirised Nowheresville, USA, and everyone now knows what happened next,” concluded Mason, as our tour finished beside a dimly lit tavern where the first beers of the day were being poured. “What many fans don’t realise is our weirdness and wit are part of the bigger story – and that’s Portland at its finest.”

Mike MacEacheran was a guest of Travel Oregon.