An imaging connection device is provided for use with a vehicle and a trailer. The vehicle includes a hitch assembly, a wired vehicle interface, and a vehicle communications unit, and the trailer includes a tow assembly and a wire harness. The imaging connection device includes a housing defining a first connector configured to mate with the wired vehicle interface and a second connector configured to mate with the wire harness; a connector interface at least partially arranged within the housing and extending between the first connector and the second connector; a camera unit at least partially arranged within the housing and configured to capture image data representing a side view of the hitch assembly; and a wireless communications unit at least partially arranged within the housing and configured to transmit the image data captured by the camera unit to the vehicle communications unit for display on a display device.