To explore the dynamic shear property of sand–irregular concrete interface, a series of direct shear tests were conducted under dynamic normal loading. These tests were designed with various joint roughness coefficients (JRC), amplitudes and frequencies of dynamic normal loading. DEM models were established to analyze the microscopic mechanical behavior. The research results indicate that a larger amplitude and frequency of the dynamic normal loading would lead to a decrease in the interface shear stress and dilation. As the JRC increased, the interface shear strength first increased and then decreased, and the dilation increased. A rougher surface would reduce the phase shift between peak shear and normal stress. The phase shift between normal stress and friction coefficient was always half a normal loading cycle. A greater JRC would activate a more violent particle motion and a thicker shear band. The increase in effective roughness would lead to an increase in the deviation angle of the anisotropic direction. The evolution of force chains was observed in three-dimensional space. Weak force chains were screened out during the shearing process. As the shearing developed, the number of force chains decreased, the average length and strength of force chains continued to increase.