In Sleepy Hollow, the gang investigate the legendary Headless Horseman, when he shows up at a Halloween costume party at Crane Manor.
A raging Halloween party is happening at a fancy mansion. Outside, in the foggy night, a horesman rides by, a grinning pumpkin for a head! The mansion is the huge and studious Crane Manor, and Mystery Inc. has been invited by Mrs. Crane to the Halloween Party. Scooby Dum, Scooby's cousin, is also there with Mystery Inc. Fred, Daphne and Velma bob for apples and Shaggy and Scooby are hitting up the buffet table, as usual.
Scooby, Shaggy and Scooby Dum encounter the Headless Horseman outside and run back inside to tell the others. Daphne, Fred and Velma are in the library with Mrs. Crane's niece, Beth. Beth mentions her great-great grandfather was Ichabod Crane. Scooby and Shaggy run in and tell their story, and Beth fears that the Headless Horseman has come back to haunt her family, considering her grandfather Ichabod was chased by one years earlier. Back on the party floor, the Headless Horseman makes an entrance causing havoc. He claims he wants a head. The Horseman scares away the guests, but not Mystery Inc.
The gang split up to look for clues. Velma, Scooby, Scooby-Dum, and Shaggy search upstairs. They start looking into rooms, but find nothing. Velma returns downstairs and Shaggy, Scooby and Scooby Dum run into the Headless Horseman who gives chase. Shaggy and the two cousins run downstairs to tell the gang, but when they all return upstairs, the Horseman is gone. Mrs. Crane is nearly grabbed by the Horseman and Mystery Inc. tries to comfort her, when a man appears and explains that the Horseman is not after her head, but is after Mrs. Crane's necklace. Beth says this is her cousin Elwood. Elwood states that ever since Mrs. Crane brought the necklace into the house, the Horseman has been appearing. Elwood makes an exit and Daphne, Fred, Velma, Scooby, Shaggy, and Scooby Dum get to work.
Elwood takes Mrs. Crane's necklace to the bank and the gang watches him drive away, and witness the Horseman ride by and snatch Elwood's head off and place it on his own shoulders! The Horseman disappears afterwards. The gang looks around Elwood's wrecked car and finds a small picture of Elwood with glue on one side, the ignition keys missing, and a newspaper clipping that tells about a flying saucer spotted at a beautician's convention. They bump into Tarlof, Mrs. Crane's butler. He explains that someone chopped a tree down and it fell on the power lines cutting the power to the mansion, and he was walking to the neighbor's to complain. The gang go to where the Headless Horseman is supposedly buried. Fred and Velma figure it out and race to the airport. Sure enough, the headless horseman is there, about to take off in a plane. Scooby and Shaggy accidentally hop on the plane with the horseman and manage to elude him as the plane soars through the air. Finally the plane wrecks and the Headless Horseman is unmasked as Cousin Elwood. He was after Mrs. Crane's diamond necklace all along, so he made up the horseman to trick Mrs. Crane into believeing the necklace was cursed. Elwood was taken to jail by the Sheriff.
The clues are explained as well, the missing keys, Elwood grabbed them out of habit when he left the car, and the picture was a passport photo for Elwood to fly out of the country. And another thing, Elwood was lying when he said he called the bank, because the butler said the phone lines were down. Shaggy found the biggest clue; on the other side of the clipping, it reads that APEX, Elwood's shoe company, had filed for bankruptcy, so he tried to steal the diamonds.
- Beth Crane (single appearance)
- Gertrude Crane (single appearance)
- Tarlof (single appearance)
- Sheriff (single appearance)
Monsters and other villains:
- Headless Horseman's horse (single appearance)(no lines)
- Ichabod Crane (single appearance)(portrait)(deceased)
Food and objects:
|Tarlof||His hands were ghostly white just like the Headless Horseman's.|
|Elwood Crane||Told his aunt about the Headless Horseman who was after her necklace.|
|Elwood Crane as the Headless Horseman||To steal his aunt's diamond necklace when his company went bankrupt.|
- Mystery Inc. all are wearing different Halloween costumes:
- Velma: Witch
- Fred: Pirate
- Daphne: Fairy princess
- Shaggy: Vampire
- Scooby and Scooby-Dum: Horse
- At the time this episode aired, "Sleepy Hollow" did not exist geographically. The village of Sleepy Hollow located in Westchester County, New York then, was known as North Tarrytown. The name was changed in 1996.
- The closest airport to Sleepy Hollow, NY is the Westchester County Airport in White Plains.
- Elwood Crane was likely inspried by Brom Bones (whether he actually existed or was a fictionalized character made for the Washington Irving story is irrelevant) who dresses up like the headless horseman in order to scare Echibod Crane away.
- In this episode, the Headless Horseman wears a jack-o-lantern for a head. The basic premise for this came from the original story, where Brom Bones dressed up like the headless horseman and used a regular pumpkin to simulate a head that he later threw at Echibod Crane across the bridge. This was built upon in the Disney adaptation, where in order to fit Disney's style better, the regular pumkin was changed to a flaming jack-o-lantern. While in neither of these did he actually wear them, it has since become the standard image for the headless horseman to wear a grinning jack-o-lantern for a head.
Animation mistakes and/or technical glitches
- None known.
Inconsistencies/continuity errors and/or goofs/oddities
- In this episode, Shaggy mentions that Scooby Dum is Scooby's brother, although this was corrected when he later referred to them as cousins; it had already been established in a previous episode that Dum and Doo are cousins.
- The Ichabod Crane described in the Legend of Sleepy Hollow did not start a family before he disappeared (he failed to marry the woman he was courting). It could be assumed the Washington Irving story fictionalized some details.
- When Velma says Shaggy found the most important clue, Shaggy says "yeah" in his normal voice, and then says, "I did?" in another voice.
- Sleepy Hollow looks nothing like it does in the episode though large mansions like the one seen in the episode do exist in that part of Westchester County.
- Modern viewers will be puzzled about the phone call clue as they will likely go "But he could have used a cell phone to call the bank." The first commercially available cell phone didn't became available until 1983, five years after this episode was first aired.
- Scooby Doo: Volume 3 VHS released by Kids Klassics in 1986.
- Scooby-Doo: The Headless Horseman of Halloween VHS released by Turner Home Entertainment on September 10, 1996.
- Scooby-Doo's Spookiest Tales DVD released by Warner Home Video on August 21, 2001.
- The Scooby-Doo!/Dynomutt Hour: The Complete Series DVD set released by Warner Home Video on March 7, 2006.
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