A costume party in Sleepy Hollow gets interrupted by the most infamous resident of the locale, the horrifying Headless Horseman. The gang and Scooby's cousin, Scooby-Dum, set off on the case, and it gets more important than ever when the Headless Horseman apparently takes the head of one of the guests.
This episode includes examples of the following tropes:
- Berserk Button: One of the few things Velma does not tolerate from any of her friends is complete and utter cowardice.Velma: He's [the Headless Horseman] right around the corner. We've got him now.Shaggy: [moaning] But I don't want him.Velma: One thing I hate is a coward. Now get going!
- Chekhov's Gun: Elwood claims that he and the bank manager share a hobby of flying airplanes. Elwood tries to use his piloting skills to escape after stealing his aunt's diamond necklace.
- Darker and Edgier: This episode remains one of the classic era's creepiest showings for a reason. Not only does it feature a real-life mythical ghost rather than an original character crafted for the series, but in one particular scene, how the ghost came to be is described in quite a gory detail higher than the usual standards of the show. Then there's the implied death of Elwood Crane, a scene leading viewers to believe that a grisly beheading took place offscreen, as well as the legitimately scary Nightmare Face the Headless Horseman continues to have for the remainder of the episode.
- Famous Ancestor: Ichabod Crane is the great-great-grandfather of the gang's friend Beth.
- For Halloween, I Am Going as Myself: A variant; when Shaggy and the Scoobys come running in, claiming to have seen the Headless Horseman, Fred theorizes that they saw one of the guests. When the actual Horseman turns up, he quickly makes it clear that he's not (meant to be) a human in costume.
- Headless Horseman: Who do you think is the spook of the week?
- "I Can't Look!" Gesture: Scooby-Dum covers his eyes when the Horseman's airplane almost crashes into a building.
- Insane Troll Logic: When the gang investigates the accident involving Elwood's car, Scooby finds and digs up an old newspaper clipping, which Shaggy reads and quotes the headline of the article. Likely because of the strangeness of the event, he immediately tries to connect it to the Headless Horseman.Shaggy: "Flying Saucer Lands at Beauticians' Convention". Ah, heh, zoinks! Pumpkin Puss is from Mars!Scooby: Ree's a redless RARTIAN! note
- Nightmare Face: The Horseman, after he gets a new head, is either bearing a sadistic grin, mad determination, a high-pitched wicked laugh or (perhaps the scariest of the lot) a chilling Death Glare to match all death glares on his morbidly pale features.
- Not a Mask: Shaggy falsely thought the Headless Horseman was wearing an Elwood Crane mask, until he snapped at him to stop pulling on his face. Nope, it really was Elwood.
- Not Quite Dead: Cousin Elwood fakes his own death to make it look like the Horseman took his head. But in this case, he was the Horseman.
- Plot Hole: Shortly after he crashes the Halloween party and sends the guests fleeing for their lives, the Headless Horseman is last seen riding away from Crane Manor on his horse, but for some reason, Scooby and the gang are looking for him inside the house in the next scene rather than going out to search the grounds.
- Pumpkin Person: The Headless Horseman has a pumpkin on his shoulders, which he's looking to replace with a head. Shaggy nicknames him "old pumpkin puss" as a result.
- Red Herring: Tarloff the butler looks scary, has white hands like the Horseman's and disappears, ostensibly to report the house's power failure using the neighbors' phone. However, he's innocent.
- Self-Deprecation: Shaggy resorts to insulting himself in an effort to keep the Horseman from taking his head, saying it's poor workmanship and doesn't fit right. The Horseman doesn't care.
- Two Men, One Dress: Scooby-Doo and Scooby-Dum wear a horse costume, with Scooby being the front end.
- Wham Line: When the search of Elwood's car comes up with almost nothing, Fred then suggests the next course of action with grim certainty, to which an unnerved Shaggy asks him why. Fred then answers with a second, more decisive line.Fred: Let's go to the cemetery.Shaggy: [laughs nervously] The cemetery? Why?Fred: Because it's time to see the grave of the Headless Horseman.
- Wham Shot: One in particular that terrifies viewers to this day, especially first-time ones who don't know much about Scooby-Doo: seeing the Headless Horseman succeed in getting a new head.
