The single wheel trailer and stabilizing hitch assembly includes a hitch which precludes lateral tilt or roll of a trailer about the longitudinal axis of the towing vehicle and trailer, the trailer having only a single wheel for support. The hitch includes a pair of horizontal plates which bear against one another, with a vertical pivot pin securing the two plates together to allow the trailer to turn laterally relative to the towing vehicle. A separate horizontal pivot axis accommodates pitch of the trailer relative to the towing vehicle while negotiating bumps and dips. However, the trailer tongue is fixed relative to the roll axis of the assembly, and the trailer cannot tilt or lean to the side while being supported by its single wheel. This greatly reduces wheel bearing and tire wear, and reduces rolling resistance of the trailer as well. Different trailer configurations are also provided.