This is a seek-and-find puzzle game in which players search for hidden items on a screen full of jumbled objects. Players follow a story based on the classic tale The Legend of Sleepy Hollow, in which the "Headless Horseman" searches for his lost head. Story sequences are displayed through still images and voiceover narrations, and occasionally contain dramatic details of violence (e.g., "Tortured and tormented, his final moments marked by…treacherous murder" and "He hadn't noticed the Hessian moving in for the kill"). Some text also contains references to characters having mistresses or affairs (e.g., "… a plan to rid him of his shrew of a wife so that she could be forever by his side" and "… a young mistress awaiting him in the woods tonight"). One line mentions a man "in his library smoking his pipe."