A series of conventional dynamic uniaxial compressive (CDUC) tests and coupled static dynamic loading (CSDL) tests were performed using a split Hopkinson compression bar (SHPB) system to explore the variable dynamic mechanical behavior and fracture characteristics of medium siltstone at a microscopic scale in the laboratory. In the CDUC tests, the dynamic uniaxial strength of the medium sandstone is rate-dependent in the range of 17.5 to 96.8 s−1, while the dynamic elastic modulus is not dependent on the strain rate. Then, this paper proposes a generalized model to characterize the rate-dependent strength from 17.5 to 96.8 s−1. In the CSDL tests, with increasing initial prestatic stress, the dynamic elastic modulus and dynamic strength increase nonlinearly at first and then decrease. The results show that two classical morphological types (i.e., Type I and Type II) are observed in the dynamic stress–strain response from the CDUC and CSDL tests. By scanning electron microscopy (SEM), microscopic differences in the post-loading microcrack characteristics in the behavior of Type I and Type II are identified. In Class I behavior, intergranular fracture (IF) usually initiates at or near the grains, with most cracks deflected along the grain boundaries, resulting in a sharp angular edge, and then coalesces to the main fracture surface that splits the specimen along the direction of stress wave propagation. In contrast, Class II behavior results from the combined IF and transgranular fracture (TF).