A tiltwing aircraft convertible between a vertical takeoff and landing flight mode and a forward flight mode includes a fuselage, a tiltwing rotatably coupled to the fuselage and a convertible tailboom and landing gear system rotatably coupled to the fuselage. The tiltwing is rotatable between a substantially vertical position in the vertical takeoff and landing flight mode and a substantially horizontal position in the forward flight mode. The convertible tailboom and landing gear system is rotatable between a landing gear position in the vertical takeoff and landing flight mode and a tailboom position in the forward flight mode. The convertible tailboom and landing gear system includes skids and linkages that rotatably couple the skids to the fuselage. The skids are positioned below the fuselage in the landing gear position and extend aft of the fuselage in the tailboom position.