A common experience while walking around Portland was coming across the uncommon. The city had some completely weird and random art displays spread throughout. Portland seems to breed or attract inventors and creators who think up the most interesting visuals and entertainment spaces.

This post highlights just three aspects of the city that I felt "keep Portland weird"— street art, people's yards, and the Kennedy School.


Street art

To give you an example of what I mean by street art, I don't mean your typical mural found in Brooklyn, NY. I mean seeing that someone spilled a bucket of blue paint on the sidewalk and then made the best of the spill by using the excess paint to draw a blue smiley face right next to it. I wish I had gotten a photo of that one. Instead, here's a picture of a fire hydrant with eyes.

I was lucky enough to have one of the most gracious hosts while I was in Portland. My host Keith, a musician and dentist, was kind enough to show me a number of different spots nearby his home in North Portland including Handsome Pizza.

On the way there one evening, he showed me Beaterville cafe. We didn't go inside—it was the outside that was important to see. Flower "beds" and old cars used as planters—this place had some of the strangest (and cleverest!) ideas for planting. But watch out! Some of these planters are old and rusty.

At this same location, there was an awesome telephone-shaped car parked on the street. What was inside on the passenger seat? A wooden duck.

Speaking of strange cars—how about this car? There was so much going on with it, I had to take multiple photos to capture its decadence.

One day, I was walking to the bus stop in Southeast Portland when I looked up and saw a shoe. The next day, I was walking down Alberta street in North Portland. I looked up and saw two shoes...??

Telephone poles were plastered with flyers from ages ago and left to naturally shed away.

Household items were personified.

And people slapped little messages like this to the public street signs all over the place.

This one I just thought was beautiful, albeit random: An industrial art piece placed on a street corner in Southeast just across the river.

People's yards

I loved walking around Portland and looking at people's yards because the most random things could be found. For instance, in a totally residential area on the way to St. John's bridge, I peered up a side street and saw a large mask propped up in someone's yard.

On another street, I came across "chicken TV." A window cut into the street side of a homeowner's chicken coop gave me a cloudy view of hens, a rooster, and...a bunny? They were all hanging out together, uncaring that big brother was watching them.

I also found this boat and enormous ship cleat in someone's yard near Forest Park. They were next to a cannon.

Kennedy School

Picture yourself walking into a classroom in your elementary school. Now imagine yourself ordering and drinking a whiskey there. Are you thinking this is just an exercise for your imagination? Think again.

This is a real place called McMenamin's Kennedy School. By far, the Kennedy School was the most unique place I went to in Portland.

Walking around the Kennedy School was like walking through a dream. A very weird dream. Many of my photos even have a dreamy vibe to them because the lighting in the place was so dim and somber. Never in my life could I imagine an establishment quite like this, but the McMenamin brothers did.

Brian and Mike McMenamin started renovating old buildings in order to connect the past with the present. They collect historic materials and interview locals to find out the history of a place before they set to work. The result is an artistic restoration of old spaces where present day activities take place and hints and reminders of the past are creatively displayed. John D. Kennedy School, a running elementary school, was closed down in 1975.

The McMenamins reopened it in 1997 as a hotel with bars, a cigar room, a restaurant, a brewery, a soaking pool, and a movie theater all inside.

As I walked through Kennedy school, whiskey in hand, I read hand-written notes passed between school children in the 1940s, observed black and white photographs of frowning teachers from the 1950s, and read yearbook messages from the 1960s. Hallways were filled with artists' commissioned pieces.

Creepy, yet beautiful paintings and murals of children playing in the school yard were reminiscent of the old photos on display throughout. Outside the Courtyard Restaurant, seating around fire pits and lights strewn from the trees offered a festive ambiance and place to socialize while peering through the old windows of a large classroom. An auditorium was gutted and antique sofas, comfy chairs, and worn out couches were brought in to create a unique seating arrangement for viewing movies.

One bar still had a chalkboard and cubby-closet installed. Another, called "the Boiler room," included abstract sculptures and wall trimmings using old pipes.

The Kennedy School was the only McMenamin space I visited, but they have several other establishments including dozens of restaurants, distilleries, hotels, and event halls located primarily in and around Portland.

This was absolutely my favorite weird place to visit—do not miss it.


There was a lot more that was weird about Portland, but I didn't always have my camera ready or think to snap a photo when I saw it. If you get a chance to visit Portland, maybe you can go on a scavenger hunt for some of the unique stuff I found—or expand on this list by finding your own!