When Brainy Smurf is favored to win the annual Smurfberry Hunt for the ninth year in a row, Gutsy Smurf sets out to discover how Brainy wins every year. Gutsy's investigation takes him into spooky Smurfy Hollow — and right into Gargamel’s trap! Can Brainy and Gutsy, with the help of Smurfette, put aside their rivalry before Gargamel captures them, or worse, will they come face-to-face with the legendary ghost, the Headless Horseman?
This animated feature provides examples of
- Art Shift: Again from 3D CGI to 2D animation, with the 3D CGI parts being used as a Framing Device for a Ghost Story which the 2D animation sequence tells.
- Bat Scare: Takes place near the end.
- Blind Without 'Em: Brainy temporarily loses his glasses after he runs away from the fake Headless Horseman and stumbles around trying to find them.
- The Cameo: Vexy and Hackus as Smurfs from The Smurfs 2. (Though in recent Nickelodeon airings, they were both edited out and replaced with two generic Smurf extras.)
- Cats Hate Water: It's not just falling into the river that Azrael hates, though.
- Chekhov's Gag: The goat that keeps eating from Vanity's cornucopia hat, which is used to become the Headless Horseman.
- Counting to Three: Azrael does this with the fingers of his paw when Gargamel leaves his hovel to go after the Smurfs just to see how long it will take for his master to return for his help.
- Dark Horse Victory: Lazy, who picked only one smurfberry during the contest, ends up being declared the winner when Gutsy and Brainy fight over who should get the medal and the medal ends up slipping out of their hands and lands around Lazy's neck.
- Do Not Taunt Cthulhu: Gargamel taunts the Headless Horseman while he is safe inside the covered bridge. He responds by throwing a flaming pumpkin at him.
- Don't Go in the Woods: Or more specifically, don't go into Smurfy Hollow.
- The Dreaded: The Headless Horseman.
- Dropped Glasses: Brainy drops his glasses during his flight from the fake Headless Horseman and ends up crawling around on his knees until he finds them again.
- Halloween Episode: To The Smurfs film series.
- Headless Horseman: One created by Papa Smurf with his magic.
- Hellish Horse: The one that the Headless Horseman rides on.
- I Feel Guilty; You Take It: Both Brainy and Gutsy felt guilty for cheating in order to get the medal for the Smurfberry Harvest contest, so they argue over each other taking what they feel the other should have...until the medal pops out of their hands and lands over Lazy's neck, declaring him to be the winner.
- Impaled with Extreme Prejudice: Thankfully averted, as Brainy lands just short of being impaled on a sharp rock after he and Gutsy fall from the cages they were held in.
- Inevitable Waterfall: Gargamel and Azrael end up going over one. Azrael even tries to warn his master about it.
- The Legend of X
- Literal Metaphor: Brainy says that the cage he's in "has Gargamel written all over it"...and we see that Gargamel's name is written on the bars of the cage.
- Literary Allusion Title: The title is one for The Legend of Sleepy Hollow.
- Mythology Gag:
- A male goat similar in appearance to Biquette from Johan and Peewit appears in this special to harass Vanity.
- In The Smurfs and the Magic Flute, Hefty is able to break a table with a single hand chop. Here Brainy tries to apply the same principle to breaking the bars of his cage, only for it to backfire and hit himself in the face.
- Place of Protection: The covered bridge serves as one from the Headless Horseman for the Smurfs as well as for Gargamel and Azrael — that is, until Gargamel decides to taunt the Headless Horseman. The Headless Horseman cannot cross the bridge, but he can still throw a flaming pumpkin into it.
- Pooled Funds: Gutsy lies down on top of a big patch of smurfberries that he found Brainy picking his smurfberries from after he scared Brainy away, looking like he's doing the backstroke.
- Removing the Rival: Gutsy accidentally caused this to happen to Brainy when he simply wanted to scare Brainy away from the secret patch of smurfberries in Smurfy Hollow so that he could win the Smurfberry Harvest contest instead of Brainy, since in Brainy fleeing away from a fake Headless Horseman he ended up being caught in one of Gargamel's traps.
- The Rival: Gutsy plays this to Brainy.
- Scary Teeth: Just what we need, a nice close-up of the few teeth that are in Gargamel's mouth.
- Smurf In A Kilt: Gutsy checks underneath the kilt when he says that he doesn't have any pants on to slow him down, despite evidence to the contrary.
- Spoonerism: Purposely invoked by Brainy: "Hey, Gargamel, you've got a nose on your wart!"
- Throw the Book at Them: Brainy does this to Gutsy when he finds out that Gutsy tricked him with a fake Headless Horseman shadow he had created to scare him.
- Vocal Dissonance: Brainy's voice actor Fred Armisen had the tendency to slip into his Speedy Gonzales voice.
- Why Did It Have To Be Bats?: Said by Gutsy as he goes through the covered bridge into Smurfy Hollow.
