Is Portland Really That Weird? An Insider’s Guide

With its motto “Keep Portland Weird” proudly displayed all over the place, the City of Roses has more than its fair share of odd, quirky, and off-beat people and places. And its residents gleefully embrace all of it. Whether you live in PDX or are planning a visit, it’s good to have an insider’s guide on hand.

At Julia Monaghan Real Estate, we have grown to know and love all the different Portland neighborhoods. Whether you like a lot of weird or just a touch of it, we can help you find the right spot. If you are ready to sell or buy in the Portland Metro area, we’re your team. Reach out today to learn more.

How Did “Keep Portland Weird” Get Started?

Any good catchphrase, nickname, or tagline should have some myths and urban legends behind it. Ironically, the Keep Portland Weird slogan has a decidedly un-weird origin. 

Having an insider's guide to Portland can help you understand what makes the city weird and quirky.

Terry Currier, the owner of Portland’s iconic Music Millennium, adopted the phrase in 2003 after learning about the Keep Austin Weird campaign from Texas. Originally intended as a way to promote and support local businesses, Keep Portland Weird grew to encompass the city’s fringe ethos.

There’s no denying this truth: Portlanders love their weirdness.

Spinoffs such as Keep Portland Wired and Keep Portland Beered have also made an appearance over the years, but they can’t compete with the original. 

Your Insider’s Guide? Just About Anything Goes

The city of Portland offers something for just about every group imaginable. No insider’s guide to Portland would be complete without recognizing the following unique and quirky aspects that help to Keep Portland Weird.

So. Much. Food

The parody show Portlandia had an episode where the characters went to a farm to meet the chickens before deciding if they could eat them or not. This dig at Portland’s farm-to-table ethos didn’t hurt anyone’s feelings.

Portlanders love their farm-to-table experiences.

The Portland food scene is impressive, diverse, and delicious. From incredible food cart pods to high-end fine dining, PDX has something for everyone.

Here are a few of the can’t-miss highlights.

Desserts Galore

Portland really loves its doughnuts. Like, REALLY loves its doughnuts. The most famous sweet shop in town is Voodoo Doughnuts, with several locations around the metro area. 

This iconic business offers more than 50 different flavors to try, and their artists are always thinking up new options. Voodoo has expanded to other markets, including Austin, TX, the town that started keeping things weird in the first place.

Voodoo is not the only Doughnut game in town, however. Our insider’s guide also includes Blue Star Donuts, where they create delectable treats with fresh spices and herbs. They have several locations around town and have expanded into California, too.

Food Carts Are Life

Food trucks and food carts used to exist only in the realm of school fundraisers and sporting tournaments. Now, however, food carts are an absolute staple of the Portland food scene.

No insider's guide to Portland is complete without a look at the food cart culture.

Permanent pods now sit throughout Portland neighborhoods, west side and east side. Some house just a few carts, while others have dozens of options. Many even include beer gardens and pet areas, further embracing Portlander life.

The city’s food carts represent an incredibly diverse array of cultures and tastes. Of course, you can find standard fare like burgers and pizza, but you also can try Hmong, Filipino, Celtic, Norwegian, and other flavors and foods. 

Insider’s Guide Tip: Farm-to-Table Is Serious Business

From food carts to fine dining, Portland restaurateurs take their job seriously. The farm-to-table movement isn’t a fad in PDX. Chefs rely on the area’s bounty when crafting their menus which means many places don’t know what they are offering until the day of.

Brick-and-mortar spots and food carts in Portland often rely on social media to get the word out about their daily menus. They see what is available from local suppliers and then post their offerings for the day.


Portland is a body-positive state with a high number of strip clubs.

As a whole, Portlanders are not Puritans. Home to the highest number of strip clubs per capita, many women-owned, PDX is comfortable with bodies. And to make sure we hit the most Portland-y vibe possible, one of the strip clubs is vegan. 

At one point, there were twice as many strip bars as public restrooms. This fact is partly because Oregon’s constitution protects “obscenity” as free speech. 

In general, Oregon ranks as a highly body-positive state, which might be why Portland is home to the world’s largest naked bike ride. About 10,000 people take part in this event each year, outside of COVID times. 

Portlanders welcome and include bodies of all shapes and sizes and don’t much care about nudity. Live and let live seems to be the common belief in this arena.

Little Oddities All Around

In addition to the big hitters in the weird category, Portland also boasts plenty of small quirky spots that even long-term residents don’t know exist.

Quirky spots around town help to keep Portland weird.

The Freakybuttrue Peculiarium is just one of those spots. An homage to all things freaky and weird, the Peculiarium even includes a large seated Krampus in lieu of the traditional Santa Claus.

If creepy stuff isn’t your vibe, you can check out the Stark’s Vacuum Museum for a tamer outing. This “museum” is all of one wall in the downtown Stark’s store with a display of 25 iconic vacuum cleaners.

One of the most entertaining sights to stumble upon in Portland is the city’s Unipiper. This unicycle-riding street performer roams the PDX streets in his Darth Vader costume, playing flaming bagpipes. None of those words are typos or mistakes. It’s all true. 

Are You Ready for a Portland Home?

Truthfully, there is so much to say about Portland’s weirdness that you’ll probably get another article on this topic from me soon. While it might not be everyone’s cup of tea, it appears to fit the bill for more and more people each day.

I’d love to chat if you’re ready to buy or sell in Portland or the surrounding areas. Our team at Julia Monaghan Real Estate knows all the neighborhoods from Mt. Tabor to West Linn, and we’re eager to help. Let’s get started!

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