It’s the star of a wildly popular TV show and boasts a food scene that puts bigger cities to shame. But, writes Barry Divola, Portland continues to fly its freak flag proudly, gentrification be damned. 

Portlandia is now in its eighth season. You wouldn’t think a television show parodying the quirks of Portland, Oregon, would have the legs to carry it that far but once you visit this city in the Pacific Northwest, you soon realise there’s a deep well of material. You also realise it’s difficult to draw the line between real life and the world of TV. Here’s a test for you. Which of the following actually exist and which are crazy ideas dreamed up by writers Carrie Brownstein and Fred Armisen for their show: (a) a vacuum cleaner museum; (b) the smallest park in the world; (c) people tethering toy horses to metal rings on the footpath; (d) a strip club where only vegan food is served? Answer: all of the above are true.

I visit Stark’s Vacuum Museum, where 25 vintage dust-busting machines, some dating back to 1905, are on display. It’s not alone in the unusual stakes – there are also Portland museums devoted to hats, BMX bikes, kayaks and canoes. I track down Mill Ends Park – the world’s smallest, according to Guinness World Records – which is about 60 centimetres in diameter and situated on a safety island in the middle of busy Pacific Highway West. In the mid-1940s, journalist Dick Fagan looked out his office window and noticed that a hole dug by city workers, intended for a utility pole, had never been filled.

What Makes Portland Weird and Wonderful

He planted some flowers then wrote a tall tale in his newspaper column about a leprechaun who lived there. For the next 20 years, until his death in 1969, Fagan would update readers on the park and it became a much-loved part of Portland life.

As I ride around on my bike – yes, I’m a hipster and this is one of the most bike-friendly cities in the country – I come across evidence of the Portland Horse Project. Back when people actually rode horses and needed to tie them up, hundreds of metal rings were bolted to the city’s pavements for this purpose, but after cars took over they started disappearing whenever roadworks were done. One resident, Scott Wayne Indiana, brought attention to the rings in 2005, tethering toy horses to them around the city’s streets. His community project captured the imagination of many Portlanders, who continue his work today, and the toy horses even have their own Facebook page and Instagram hashtag.

I don’t enter Casa Diablo, a strip club where only vegan food is served, because, um, I’m not vegan. At least that’s my excuse. But it’s there if you like a bit of tofu with your exotic dancing. It’s said that Portland has the largest number of strip clubs per capita in the United States. It also has thriving music, art, coffee and craft beer scenes, one of the world’s biggest independent bookstores in Powell’s Books and more than 500 gourmet food carts parked around the city. These eateries on wheels are packed every lunchtime and each has a specialty: authentic British fish and chips at The Frying Scotsman, grilled cheese sandwiches at The Grilled Cheese Grill and gourmet dumplings at The Dump Truck.

No wonder so many people are moving here, although that’s a bit of a sore point with locals. One night, I’m having a drink at the Doug Fir Lounge, a hip bar decorated like a hunting lodge. I get chatting to the guy next to me at the bar, who is bearded, tattooed and wears a trucker cap. He asks me what I’m doing in Portland and I tell him I’m writing a travel story. “Don’t do it, man!” he exclaims. “There’ll only be more Californians moving here and my rent will go up again! Portlandia has a lot to answer for.” 

The TV show doesn’t have to push reality too far for satire. After all, there’s a well-known local who dresses as Darth Vader and plays the bagpipes while riding a unicycle (he’s called the Unipiper, naturally) and everyone thinks that’s totally normal. Like many Portlanders, local Meghan Sinnott can’t fit everything she does on one business card: brand manager, organiser of the World Naked Bike Ride, cultural liaison for the Filmed by Bike movie festival, producer for The Moth storytelling podcast and travel guide to Portland’s quirkier side. She’s also been in a Portlandia crowd scene, which was part of an episode about a Star Trek festival in a park – and yes, before you ask, of course that really happens in Portland. “Now Portland is off the hook and people are moving here because of all the great things about the city, like good coffee, well-sourced food and being able to ride a bike to work,” she tells me. “What we have to do is make sure all those great things stay that way.”

The city’s unofficial motto is “Keep Portland Weird” and although it’s become something of a cliché, there’s plenty of truth hiding behind the phrase. Besides, it’s difficult to shake the tag when your city was named as the result of a coin toss. In 1845, city founders Asa Lovejoy (who wanted to name it after his home town of Boston, Massachusetts) and Francis Pettygrove (who was pushing for his beloved Portland, Maine) flipped a penny to decide. Pettygrove won the best-of-three toss.

As I continue to roll around town, I get the eerie feeling I’m stuck in an episode of The Simpsons. That’s because creator Matt Groening grew up here and many of his show’s characters, including Ned Flanders, Reverend Lovejoy, Mayor Quimby and Kearney the school bully, were named after the city’s streets. Groening even carved a picture of Bart into wet cement and it’s still there on the sidewalk outside his alma mater, Lincoln High School.

Look down – hiding among the paving bricks of Pioneer Courthouse Square, each one bought by a Portland citizen and inscribed with their name, you’ll find Elvis Presley, Mr Spock, Bilbo Baggins and Jesus Christ. Look up – what is that monument resembling a towering cluster of kids’ bikes attached to a pole? That’s the Zoobomb Pyle. Each Sunday night, groups of riders, many dressed in costume, take the MAX Light Rail to the Oregon Zoo, set high on a hill in Washington Park. They either bring their own child-size bike or borrow one from the Zoobomb Pyle. Once they reach their destination, they freewheel en masse down the steep streets that radiate from the zoo.

What Makes Portland Weird and Wonderful

The true quirkiness of the place was driven home when I told someone I was off to interview two professional clowns. Instead of looking at me like I was an idiot, he responded, “Oh, great, which ones?” Their names are Dingo and Olive and they get around on customised tall bikes and dress like they’ve just emerged from the pages of Alice’s Adventures in Wonderland. They’ve appeared in Portlandia three times, including the famous “The Dream of the ’90s is Alive in Portland” musical segment from the first episode.

I felt that if anyone could tell me about what makes this city weird, it would be a clown. “The weirdest and greatest thing about Portland is that we can even exist,” says Dingo. “We couldn’t do this anywhere else in the country. The hardest thing about being a professional clown is making money from it. Since 2006, I haven’t had a day job. But Portland isn’t necessarily all about quirky counterculture; it’s about being yourself. And even though Portland has changed a lot, it does still let people be themselves. Hopefully that won’t change.”

SEE ALSO: Does Portland Have the Best Coffee in the US?

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