A winding device includes a winding shaft that rotates and winds a print medium conveyed from a printing device having a conveyance roller that conveys the print medium, a gear, and a motor driving the conveyance roller and the gear. The winding device also includes a power transfer mechanism to connect to the gear and transfer power to the motor, and a lever disposed between the winding shaft and the conveyance roller in a conveyance path in a configuration in which the winding device is connected to the printing device. The lever may be moved between a first position in which the print medium bends and a second position in which the print medium bends at a shallower angle than at the first position.