Awnings are regulated by City of Toronto Municipal Code Chapter 743, Streets and Sidewalks. In order to construct an awning the building owner must apply for permission to do so from the City. If that application is approved, the owner must then enter into an encroachment agreement with the City which sets out the specifics of the proposed structure, the annual feeand which indemnifies the City.
The City is pretty protective of the sidewalk, although I think a lot of the reason has to do with the built form differences between Toronto and NYC.