The horseman is shown riding his steed, sword raised, as the horse rears on its hind legs. A dense forest of ominously bare tree branches, gravestones, and pumpkins fills the background. The inscription "HEADLESS HORSEMAN OF SLEEPY HOLLOW" is divided along the outer rim. "1 TROY OZ 999 SILVER" is found in smaller text just beneath the horse.
The site of the Headless Horseman's ghostly appearance is depicted on the reverse. The cemetery is shown in great detail against the backdrop of a cloudy night sky. The front gate is slightly ajar. Rim inscriptions read, "FAVORITE HAUNT OF TROUBLED SPIRITS" in Gothic text.
According to Irving's retelling, the horseman was a Hessian (a German mercenary) who was decapitated by a cannonball during the American Revolutionary War. The battle took place around the time of Halloween. Now, the horseman's tortured spirit haunts the church where he was buried in Sleepy Hollow, New York.