Truck activity is logically connected to vessel activity at a port. In turn, vessel activity is also influenced by truck shipments. Although one might expect a direct and straightforward relation between these two types of shipments, that is rarely the case. For instance, many maritime containers carry consolidated cargos that have multiple and different final destinations. Also, different truck capacities, customs clearance and regulations play a critical role in determining the actual relation between these two types of shipments. This project aims at shedding light on the nuances of maritime and roadway flow relations by quantitatively analyzing the linkages between these two types of shipments. The study performed a statistical analysis to determine the probability distributions of vessel and truck activity, and then explore the correlation of each activity with the other. The analysis yielded coefficients that function as explanatory values for specific truck flows. The ultimate purpose of this study is to provide a clearer and quantitative understanding of the relationship between maritime and truck shipments, and by doing so, to provide tools to develop a system for managing trucks that maximizes efficiency for industry, while minimizing industry’s negative impacts on a region. For this purpose, the study selected the Port Freeport as a case study.