The transition of waterfront land use from industrial to post-industrial is a global phenomenon. There are several forces that are driving this change, including the advancement of shipping technology and the relocation of industrial processes to areas with greater availability of land. In place of industrial uses, many cities have undertaken, or are in the process of undertaking the redevelopment of their waterfront. As a result of past industrial use, there often exists, a significant amount of transportation infrastructure that isolates the city from the waterfront. This paper establishes the context for waterfront redevelopment, before examining the impact of infrastructure urban forms by using the work of Kevin Lynch as a tool for analysis. Several case precedents are used to examine the course of action that other North American cities have pursued to mitigate the impact of infrastructure forms on the waterfront and how they may influence the way Toronto deals with its waterfront infrastructure.