The story begins with the wealthy and reckless J. Thaddeus Toad, who spends his days indulging in various fads and adventures around the English countryside. His latest obsession with motorcars leads him to trade the family estate for a stolen car, resulting in his imprisonment for theft. Meanwhile, Toad's loyal friends—Ratty, Mole, and the cantankerous Badger—work tirelessly to prove his innocence and reclaim Toad Hall from the clutches of the nefarious weasels who have taken over.

The tale then shifts to Sleepy Hollow, where we meet the lanky, superstitious schoolteacher Ichabod Crane. Ichabod arrives in the quiet village with dreams of marrying Katrina Van Tassel, the beautiful daughter of a wealthy farmer. However, Ichabod faces stiff competition from the town's burly prankster, Brom Bones. As Halloween night approaches, Brom crafts a plan to play on Ichabod's fears by telling him the legend of the Headless Horseman. This ghostly specter, rumored to haunt Sleepy Hollow, soon becomes central to Ichabod's fate as he encounters the eerie figure in a climactic chase through the haunted woods.