Inland terminals, or dry ports, have played an important role in multimodal transportation networks as transportation hubs that provide connections between seaports and hinterland economies. While important, evaluating the operational performance of a dry port is especially challenging since it depends not only on internal factors, such as the variety and number of container handling equipment (CHE) deployed, but also on other external factors, including changes in transportation policies and container demands experienced by a dry port. To properly evaluate the holistic performance of a dry port while considering all the aforementioned factors, a discrete event simulation (DES) framework is herein developed and applied to the Ladkrabang Inland Container Depot (LICD)—one of the largest dry ports in Southeast Asia—under various operational settings. Despite complicated internal operations, the devised DES framework has shown itself useful in the analyses of LICD, due largely to its flexibility that allows users to include sophisticated operational rules into models. According to our computational results, the current LICD operation is markedly ineffective as the usage rates of all CHE types are relatively low and varied across gate operators—especially the yard truck whose values range between 2.46% and 11.15% on yearly average. We also find that, by redesigning the LICD and its internal operations, the LICD’s performance could be substantially enhanced—even with fewer numbers of CHE. Regarding the four CHE types, the reach stacker seems to limit LICD’s capability, as its utilization tends to first reach the maximum allowable rate of 75%, while the rubber tyred gantry crane could help boost the usage rate of yard trucks, which, in turn, results in reduced container dwelling times. Nonetheless, the modified LICD could accommodate up to 140% of the current container demand before it experiences operational difficulties induced by the saturation of container flow from rail transportation.