A docking station is provided. The docking station has an engagement member, a coupling detector, a connector, an advancing and retracting mechanism, and a controller. The engagement member can be inserted into an engagement hole of a portable information device. The coupling detector detects whether or not the engagement member has been engaged with the engagement hole. The connector can be connected to a connection terminal provided in a side surface of the portable information device. The advancing and retracting mechanism is operated by the driving force of a motor to advance and retract the connector to connect and separate the connector to/from the connection terminal. The controller operates the advancing and retracting mechanism when it is detected that the portable information device is coupled with the docking station to advance the connector to connect the connector to the connection terminal.