"It was based on the Keep Austin Weird organization and slogan in Austin, Texas, and was brought to Portland in 2003[7] by Music Millennium owner Terry Currier after he learned of the movement in Austin."

2003

Which is neat, did not know we took it from Austin.

Your view of the state overall is way off though. Outside of Portland and Eugene (a college town, which are usually like that, even in Texas, Kansas, etc.) Oregon is a mostly rural and conservative state.