Our understanding of soil deformation processes, especially its dynamics, remains limited. This hampers accurate predictions of the impact of soil management practices such as agricultural field traffic on (physical) soil functions. The main objective of this study was to investigate whether seismic measurements could be used to assess the dynamic soil behavior during repeated loading. Moreover, we aimed at linking the velocity of P-waves, Vp, to traditionally measured soil properties associated with soil compaction, namely bulk density (ρb) and penetrometer resistance. A wheeling experiment was performed with an agricultural tire (60 kN wheel load) on a gleyic Cambisol. We measured Vp using an acoustic (microseismic) device at various depths before, during (i.e., below the tire), and after wheeling. In addition, we measured bulk density and penetrometer resistance before and after wheeling, and simulated the evolution of bulk density due to the wheeling using a soil compaction model. The dynamic soil response during loading–unloading–reloading cycles could be well captured with the seismic method. The measured Vp related to bulk density, and the compaction-induced increase in Vp correlated with the increase in penetrometer resistance. The seismic measurements seem a promising in situ method for gaining new insights into the dynamics of soil behavior. The method may be especially powerful when combined with traditional measurements and with modeling of soil deformation.