A trailer assembly is disclosed that is operable to transport vehicles. The trailer assembly includes at least two tires and a first frame section, a second frame section, and a third frame section. The tires are coupled to the first frame section. The second frame section includes a platform configured to support at least a front wheel of a vehicle. The second frame section and the third frame section are each rotatably coupled to the first frame section. The third frame section includes a portion adapted to be directly selectively couplable to a trailer hitch of an automobile. A winch assembly couples the second frame section to at least one of the first frame section and third frame section. The winch assembly is operably configured to both lower the second frame section and raise a portion of the first frame section independent and without rotation of the third frame section.