An image pickup system including an image pickup device and a connection device is provided. The image pickup device includes an image pickup unit which picks up a subject image, a display unit, a first character image generation unit, and a first control unit. The first character image generation unit generates a first character image representing one or more characters to be displayed on the display unit. The first control unit outputs the subject image and information representing the above-noted one or more characters to the connection device when the image pick-up device and the connection device are connected with each other. The connection device includes a second character image generation unit. The second character image generation unit generates a second character image representing one or more characters to be displayed on an external display device, based on the information representing the above-noted one or more characters.