Computer based simulation models have often been used to study the multimodal freight transportation system. But these studies have not been able to dynamically couple the various modes into one model; therefore, they are limited in their ability to inform on dynamic system level interactions. This research thesis is motivated by the need to dynamically couple the multimodal freight transportation system to operate at multiple spatial and temporal scales. It is part of a larger research program to develop a systems modeling framework applicable to freight transportation. This larger research program attempts to dynamically couple railroad, seaport, and highway freight transportation models. The focus of this thesis is the development of the coupled railroad and seaport models. A separate volume (Wall 2010) on the development of the highway model has been completed. The model railroad and seaport was developed using Arena® simulation software and it comprises of the Ports of Savannah, GA, Charleston, NC, Jacksonville, FL, their adjacent CSX rail terminal, and connecting CSX railroads in the southeastern U.S. However, only the simulation outputs for the Port of Savannah are discussed in this paper. It should be mentioned that the modeled port layout is only conceptual; therefore, any inferences drawn from the model's outputs do not represent actual port performance. The model was run for 26 continuous simulation days, generating 141 containership calls, 147 highway truck deliveries of containers, 900 trains, and a throughput of 28,738 containers at the Port of Savannah, GA. An analysis of each train's trajectory from origin to destination shows that trains spend between 24 - 67 percent of their travel time idle on the tracks waiting for permission to move. Train parking demand analysis on the adjacent shunting area at the multimodal terminal seems to indicate that there aren't enough containers coming from the port because the demand is due to only trains waiting to load. The simulation also shows that on average it takes containerships calling at the Port of Savannah about 3.2 days to find an available dock to berth and unload containers. The observed mean turnaround time for containerships was 4.5 days. This experiment also shows that container residence time within the port and adjacent multimodal rail terminal varies widely. Residence times within the port range from about 0.2 hours to 9 hours with a mean of 1 hour. The average residence time inside the rail terminal is about 20 minutes but observations varied from as little as 2 minutes to a high of 2.5 hours. In addition, about 85 percent of container residence time in the port is spent idle. This research thesis demonstrates that it is possible to dynamically couple the different sub-models of the multimodal freight transportation system. However, there are challenges that need to be addressed by future research. The principal challenge is the development of a more efficient train movement algorithm that can incorporate the actual Direct Traffic Control (DTC) and / or Automatic Block Signal (ABS) track segmentation. Such an algorithm would likely improve the capacity estimates of the railroad network. In addition, future research should seek to reduce the high computational cost imposed by a discrete process modeling methodology and the adoption of single container resolution level for terminal operations. A methodology combining both discrete and continuous process modeling as proposed in this study could lessen computational costs and lower computer system requirements at a cost of some of the feedback capabilities of the model This tradeoff must be carefully examined.