Where I live in Seattle, Capitol Hill, is considered by most to be the counterculture enclave in the city. You're more likely to find some of the most 'colorful' citizens of Seattle in this area; nobody cares or notices if a person is a crossdresser, gay, straight, dressed in nothing but a leather speedo, tattooed and pierced to the nines....you get the idea. Having lived in this environment for some time now, I find it difficult to leave. I moved to the suburbs of the city last year and only lasted 6 months; I missed the melting pot of people, the chaos, and the people watching. I know for many people its sometimes bizarre or even uncomfortable, but I wouldn't have it any other way.
That being said, does your city have an area most associate as being similar? I'm curious when I travel around the country where that may be. Obviously some cities are just more 'out there' in general, but that doesn't mean a place a person may associate with being reserved doesn't have its areas.
If you have pictures, all the better!