The Highwayman is a character that appears in The Songs of the Dark Lantern alongside other characters in the Tavern Keeper's tavern. He is, as his title implies, a highwayman and wears a black mask and red gnome-styled clothes. He is the first character in the tavern shown, as he stands in the top floor window staring down on Wirt, Gregory, and Beatrice. He interrupts Wirt's explanation of how he and his brother got lost and performs "The Highwayman Song" in the tavern, during which the camera takes on the characteristics of a fisheye lens. The toymaker has a toy representing him that can be seen in the opening song.
He is voiced by Jerron "Blind Boy" Paxton.
The highwayman first came across Fred the horse when he robbed a carriage driver on St. Leonard's Bridge and the horse followed the driver inside the covered bridge. The highwayman threatened Fred into giving him the load he'd been pulling down the river. He also made Fred promise not to tell anyone what he'd seen.
Later, after Fred had been forced to tell a judge that the highwayman had stolen his load, Fred returned to St. Leonard's Bridge. Fred felt someone on his back, and it was the highwayman. Since Fred had told the others what happened, the highwayman took Fred as his horse, forcing him to become an outlaw like himself.
- In slang, a "Highwayman" is a criminal who steals from travelers. This is referenced in Over the Garden Wall by having the Highwayman display interest in stealing and other criminal activities, but also in Fred, who was the Highwayman's horse, which explains Fred's desire to steal shown in "Mad Love".
- The Highwayman might be or might be based on a redcap, a vampiric, killer imp of English folklore that takes up residence in abandoned castles. They murder travelers unfortunate enough to stray into their domain and dye their hats with the blood of their victims. They need to do this for if the blood dries, they will die. They are described as small, grizzled men with red eyes and large teeth. The highwayman appears to have some physical qualities of a redcap.