The objective of the proposed study is to develop a simulation model that will be capable of ascertaining the interactions between the marine terminal operations and a highway system that provides access to the port. The model will be specifically focusing on the underlying relationship between the changes in the wharf operations caused by large ships and their schedules, and resulting peak truck demand on regional highways, along with the distribution of truck arrivals and departures at the port’s gates. In addition, a set of operational and policy improvements will be defined to address the deficiencies of the highway system in handling the growing and evolving port-related truck demand. These improvements will be formulated in the simulation model as well, allowing the planners to evaluate the effectiveness of each improvement. Ultimately this model would be used as a decision-support tool in analyzing alternative capital strategies to address port intermodal connectivity, regional highway and freight mobility in the context of port growth, and economic competitiveness of a region from a freight transportation service aspect.