A site management system includes an unmanned airplane being switchable between an airplane mode for high speed flight and a VTOL mode for low speed flight, a working vehicle working in a civil construction site, a shape detection sensor provided in the unmanned airplane to detect a shape of the civil construction site, and an external control apparatus that controls flight of the unmanned airplane, driving of the working vehicle, and driving of the shape detection sensor. The external control apparatus moves the unmanned airplane to an observation area by performing the high speed flight. Further, the external control apparatus detects a shape of the observation area by driving the shape detection sensor while performing the high speed flight or by driving the shape detection sensor while performing low speed flight by switching from the airplane mode to the VTOL mode.