Abstract: A trailer connecting guide for use with a boat trailer or the like. The trailer connecting guide is attached to one side of the tongue of the trailer and is operable to guide the trailer sufficiently close to the tow vehicle to complete the connection. The trailer connecting guide assembly includes a pulley, a mounting bolt, and a winch cable guide. The cable guide is mounted between the pulley and trailer tongue and includes at least one elongated slot adjacent to the pulley track which restricts the lateral movement of the winch cable with respect to the pulley track to prevent the winch cable from pumping out of the pulley track. In operation, a length of cable is first let off the winch and the end of the winch cable is attached to the towing vehicle adjacent the vehicle hitch. A portion of the cable is then slipped around the pulley and guide assembly and any excess slack in the cable is taken up by operation of the winch.