Vehicle chocking systems include a first chock comprising a first bottom surface, a first front wheel restraining surface and a first rear wheel restraining surface opposite the first front wheel restraining surface, a second chock comprising a second bottom surface, a second front wheel restraining surface and a second rear wheel restraining surface, wherein the first bottom surface, the first front wheel restraining surface and the first rear wheel restraining surface of the first chock and the second bottom surface, the second front wheel restraining surface and the second rear wheel restraining surface of the second chock each comprises a proximity sensor, wherein the proximity sensors are communicatively coupled to a controller comprising a processor and a memory having a computer readable and executable instruction set to determine if the proximity sensors for each of the first bottom surface, the second bottom surface and opposing wheel restraining surfaces are engaged.