Winnipeg has a major spiritualist part to it's culture that I've noticed. I don't even think the natives know how far it goes, so Free Spirits are fairly free to go around in Winnipeg as long as laws aren't being broken.
Also, I figure that "The Forks Market" would have a strong positive emotional environment to it, which leaks into the Astral Plane, and attracts Free Spirits. I certainly feel it around the place, it's a very calming and soothing place, yet ancient and... Hard to describe in words. Timeless is the best I can use to describe it, despite the combination of old and new buildings, I wouldn't be surprised if I walked around a corner and saw some classic (New France Colonial Era!) Voyageurs looking around for some tanned skins.
That said, Free Spirits aren't recognized legally in any way, so they have freedom, but no protection either. On the flipside, they don't have to pay the Busker Fee.