Jude Acers in New Orleans (at least 35 years). World's most famous street chess player.
Photo credit: Derek Bridges
Joe Smolij, Toronto's most famous street player (from the 1960's to the 1980's) Many stories about Joe Smolij at some point I'll add one or tell me yours.
Photo credit: Norman Bolduc
These are the most basic form of outdoor chess "tables" basically just chess boards attached. There are several of these, most of them graffitified, outside OISE (teacher's College) at the corner of Bloor and Spadina.