So my hometown's 'tagline' is "keep Portland weird." Which means, it's pretty weird. This is a bit of a challenge set up by @danidee .
For the first thing which makes my hometown weird, is the BrewCycle. It's a local, multi-person powered bycicle. The bike is always full of people who are talking and drinking beer, while pedling down the streets of Portland. There's even a bartender in middle of the bike, serving people!
As shown above, the "Darth Vader Riding a Unicycle While Playing Some Flaming Bagpipes Guy." This dude rides around Portland playing some tunes on his flaming bagpipe. Possibly the weirdest attraction here.
Now this guy, is something special. He totally pimped out his van with crazy sculptures and designs, and painted it all gold. He is known to drive around the streets of downtown portland, although I have only seen him once. He calls his vehicle the "Never Never Van."
Voodoo Doughnut. You may have heard of it. Voodoo makes donuts with the craziest toppings you can think of, like bacon, or cereal. Flavors can range from chocolate (a very rare flavor at Voodoo) to cranberry to peanut butter. I'm not a huge fan of their donuts, but Voodoo is a huge tourist and local attraction, with lines to get inside usually around the block.
I would add a few more things, but I made this post using my phone, and it took a while. So excuse spelling mistakes if you see any ;). That said, these are the most popular weird attractions throughout Portland!