During one of my first trips to Portland, my friend bought me a tarot reading from a guy sitting on the sidewalk. He was minding his own business, busy entertaining the passersby with music from his tambourine. I forgot what he told me my future would be, but I remember thinking that was THE weirdest thing I'd probably ever seen. That's how weird Portland is, and I love it!

We were on our way to take our then-three-year-old kids to Playdate PDX, in what I later learned was the trendy neighborhood of the Pearl District. I couldn’t get enough of all the trendy Portland neighborhoods. I want to visit them all! If you are planning a trip to visit Oregon, keep reading to find out the most popular trendiest Portland neighborhoods to visit. Who knows, you might be lucky enough to stumble upon your own sidewalk tarot reader someday!

Keep Portland Weird Sign
The Keep Portland Weird Sign located at Burnside St and 3rd Ave, Credit: Janne Simoes on Unsplash

Portland labels everything with the trendy “PDX” label. I have never seen a city take something as mundane as the airport code and turn it into something hella cool, but if anybody was to do it, it would be PORTLAND! 😂


The Portlandia television show on the IFC network
Portlandia via Facebook

Portland has a quirky vibe to it, but the show Portlandia is an over-the-top version of the city. For instance, the Mayor of Portland is not a clueless goofball like portrayed by Washington state native, Kyle MacLachlan, who was a parody of Portland's then-Mayor, Sam Adams.

🌹Ted Wheeler is the current mayor of Portland.

Ted Wheeler is the current mayor of Portland.
Tom Wheeler, Politician via Facebook

SEE ALSO: 10 Things Yakima Is Known For: The Good, The Bad, and the Ugly


(See my above story about the sidewalk tarot reader.)

5 Trendiest Popular Neighborhoods in Portland

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