A drying device includes a drum, a contact conveyance roller, and a cooling device. The drum heats a continuous medium while conveying the continuous medium. The continuous medium is wound around a circumferential surface of the drum. The contact conveyance roller contacts the drum at a downstream end of a portion of the continuous medium wound around the circumferential surface of the drum in a conveyance direction of the continuous medium. Further, the contact conveyance roller conveys the continuous medium separated from the drum. The continuous medium is wound around the contact conveyance roller. The cooling device cools the contact conveyance roller.