A Halloween party at The Crane Manor in Sleepy Hollow begins a mysterious adventure for Scoobies Doo and Dum and the gang, when the legendary Headless Horseman shows up as an uninvited guest. A newspaper clipping and a photograph lead the sleuths and The Scooby Cousins to the airport, where the Horseman attempts to make a break for it in an antique biplane. A midair caper, with The Scoobies, Shag, and The Horseman aboard, results in the zany conclusion of the case: Cousin Elwood Crane’s company had filed for Chapter 11 bankruptcy and tried to steal Aunt Gertrude Crane’s diamond necklace, blaming this fiendish feat on the legendary Headless Horseman. Scooby-Dum continues to look for clues, turning up an angry goldfish in the pond!