The Port of Oakland (“Port”) is the 5th largest container seaport by volume in the U.S. and the largest in Northern California. Maritime shipping activity at the Port exceeds 2 million import and export twenty-foot equivalent unit (TEU) containers annually. Containers may be full or empty, but nonetheless typically require hinterland shipment and intermodal transfer between maritime and land-based freight distribution systems. The freight trucking mode (“drayage”) handles approximately 80% of all TEU throughput at the Port, thus constituting the majority of landside Port traffic. The Port is also situated adjacent to dense urban development thereby exacting certain external impacts. Drayage impacts on regional roadway infrastructure proximate to the Port are explored, to expand knowledge of freight network conditions and relevant policies addressing the topic in the San Francisco Bay Area. Statistical regression analysis and elasticity results estimate a certain level of impact on nearby freight corridors of I-80, I-680, and I-880. Drayage traffic has continued to increase since 2000, as a function of increasing TEU throughput occurring at the Port. Policies to address stable freight flow and infrastructure maintenance are ongoing, although additional studies are also recommended to ascertain comprehensive network impacts.