A vehicle trailering system comprises a towing vehicle comprising a hitch mounting mechanism, and a trailer connectable thereto. The trailer comprises a body defining an interior space sized to fit at least one vehicle and having first and second sets of spaced-apart carrying members attachable to opposite sides of the body, thereby defining respective first and second loading levels. The trailer further comprises a gate movable between the first and second levels along first and second support members. First and second connecting members are respectively attachable to the gate and are operable to movably carry the gate with respect to the first and second support members. The system further comprises an actuator system connected to a synchronization system, which are operable to synchronize the movement of the first and second connecting members along the respective longitudinal lengths of the first and second support members. Associated trailering methods are also provided.