Rather than a tragedy as one might expect from the title, the climax of "The Legend of Sleepy Hollow" contains a bit of irony or even humor. Prior to the climax, the author paints Ichabod as a less than honorable, rather strange man in pursuit of Katrina, a young and beautiful woman who is also pursued by Brom, a handsome bachelor. After being invited to a party at Katrina's, Ichabod who thought he might have a chance at winning Katrina's heart, realizes that he does not. As Ichabod rides out of town after leaving Katrina's party when she disappoints him, he finds the path dark and the woods frightening. Along the path he sees a dark figure that begins to chase him. Looking behind him during the chase, he realizes the figure on the horse is headless and assumes it is the dreaded "Headless Horseman" of local legend. Ichabod continues to attempt to outrun him but the headless figure on the horse in the final moments of the climax, throws his head at Ichabod, striking him in his own head and knocking him off his horse. It turns out that the head was but a pumpkin.
The climax of the story comes toward the very end when Ichabod is on his final ride through Sleepy Hollow. After Brom and the other guests have marveled each other with ghost stories, Ichabod sets out on his ride home, but his over active imagination begins to eat at him as he remembers the local ghost stories. He begins to sense someone following him and he believes it to be the Headless Hessian. He quickens his pace to try and lose him, but he he finds he cannot escape. Ichabod remembers the headless horseman about to throw his head at him and then he is knocked unconscious by the "head" which was a pumpkin.