In one aspect, a method for compressing crop material for ensilage may include monitoring, with a computing device, a location of a work vehicle within a silage heap as the work vehicle traverses a layer of crop material within the silage heap. The method may also include determining, with the computing device, a current density of the layer of crop material as the work vehicle traverses the layer of crop material. Furthermore, the method may include controlling, with the computing device, an operation of the work vehicle based on the monitored location and the determined current density such that the work vehicle compresses the layer of crop material.