Interactions between the aerodynamics and dynamics of bluff bodies are important in many engineering applications, including suspension bridges, tall buildings, oil platforms, wind turbine towers, air drops, and construction with cranes. In the rotorcraft field, bluff bodies are commonly suspended underneath the vehicle by tethers. This approach is often the only practical way to deliver a payload in a reasonable amount of time in disaster relief efforts, search-and-rescue operations, and military operations. However, currently a fundamental understanding of the aerodynamics of these bluff bodies is lacking, and accurate dynamic simulation models for predicting the safe flying speed are not available. In order to address these shortcomings, two main advancements are presented in this thesis. The aerodynamics of several three-dimensional canonical bluff bodies are examined over a range of Reynolds numbers representative of wind-tunnel-scale to full-scale models. Numerical experiments are utilized, with a focus on uncertainty analysis and validation of the computations. Mean and unsteady forces and moments for these bluff bodies have been evaluated, and empirical models of the shear layer characteristics have been extracted to quantify the behaviors and provide predictive capability. In addition, a physics-based reduced-order simulation model has been developed for bluff bodies. The physics-based approach is necessary to ensure that the predicted behavior of new configurations is accurate, and it is made possible by the breakthroughs in three-dimensional bluff body aerodynamics presented in this thesis. The integrated aerodynamic forces and moments and dynamic behavior predicted by model are extensively validated with data from wind tunnels, flight tests, and high-fidelity computations. Furthermore, successful stability predictions for tethered loads are demonstrated. The model is applicable to the simulation of any generic bluff body configuration, is readily extensible, and has low computational cost.