During the last two decades urban redevelopment of waterfronts has accelerated. The historical significance of these areas coupled with their unique visual amenities has resulted in major renewal efforts in many cities. The competition between the waterway navigation industry and redevelopment interests for scarce waterfront land has resulted in conflicts. Congestion along the access routes to existing ports and terminals has affected the efficient movement of goods to and from the waterfront. The results of an investigation into waterfront redevelopment issues and port and terminal landside-access conflicts are presented. There are many complex forces at work that affect the use of and access to waterfront land. Some of these forces are economic and involve uses of the waterfront that are the “best and highest,” one example of which is river-boat gaming. The surveys and case studies conducted identified many conflicts that have occurred. Guidelines have been developed that address some of the problems that arise during the development of waterfront development projects and planning of adequate transportation access. Application of these guidelines by waterway transportation interests, urban planners, transportation engineers, and community officials may alleviate some of the conflict and enhance the planning process.