A figure known as the Headless Horseman, thought to have been a soldier whose head was ripped off by a stray cannon ball, is said, by night, to ride the countryside by Sleepy Hollow, in search of a new head. One Halloween night, schoolmaster Ichabod Crane took a wrong turn in the woods, and ran afoul of the murderous ghost, whom he fled to the Bridge of Souls, inaccessible to the Horseman, but didn’t make it, never to be seen again. Legend holds the two ghosts to resume their chase each Halloween night.
Ian Matthews, having just moved to Sleepy Hollow, steps onto the school lawn, Katie, carrying a box of decorations for tonight’s Halloween dance, is bumped by ex-boyfriend Brad, and drops her quarry.
Ian hastens to assist, and in the gym, helps with the decorations.
That night, garbed in eighteenth century attire, Ian arrives in the thriving gym to find Katie, in a feminine variation thereof. Brad, garbed as a pirate, makes a point of knocking into Ian. He and Katie laugh off the tension with a dance.
At the drinks table, Brad tries to reignite his relationship with Katie. Ian suggests Brad desist. Brad roughly drags him outside.
Outside, Ian guardedly raises his fists. But Brad has something else in mind. He recounts the local legend, where, in the woods, Ichabod Crane took a wrong turn, whereupon the Headless Horseman threw a pumpkin at him and took his head. For initiation, like Brad and friends all did, Ian must go into the woods to get the pumpkin. It’s either that, or fisticuffs.
Ian decides to humor them. As directed, he takes a path through the nearby woods, and comes to a fork in the road. As he turns left, he hears the distant neigh of a horse.
On the wooden bridge, he finds the pumpkin, lit from within by a green glow stick. He picks it up, and hears a distant laughter. A figure in a flowing black cloak, with no head, draws a sword.
Ian runs, and the figure runs after him. Ian drops and begs for his life. The "Horseman" raises his frame-mounted coat, and Brad emerges to laugh in triumph. He beckons Katie, who decidedly prefers Ian.
Cheered by an offer to walk Katie home, Ian lends her his jacket. In the distance behind them, on horseback, meanders a cloaked figure, with no visible head...
As they walk, Katie and Ian hear distant whinnying. They peer behind them, and turn to find on the path, atop a white horse, an ashen-faced man in eighteenth century clothes. With quaint courtesy, he brightly greets them, and requests directions to the Bridge of Souls. Ian directs him to the left fork. He gratefully rides off, and introduces himself as Ichabod Crane, the new schoolmaster.
At Katie’s front door, Ian suddenly remembers to have left his bike at school, and bids Katie good night.
On the school lawn, he hears neighing. He realizes to have left the key in his jacket. With a startled cry, he finds Katie to have followed him, on her bike, with the jacket. As Ian unlocks his bike, Katie sees, on the school wall, an enormous shadow of a man on horseback.
Ian tells Brad to stop this nonsense. As he approaches the shadow, he realizes that nothing appears to be casting it. He then sees a smaller version of the shadow, which now includes, in place of a head, what looks like a pumpkin. With a flash of ethereal flame, the shadow bulges forth into the solid form of a large black horse, and black-cloaked, sword-wielding, pumpkin-headed rider. The Horseman charges.
Ian urges Katie to ride. The Horseman tosses aside the pumpkin, revealing the vacancy above his shoulders. Katie gets the point. They ride for their lives. Brad, in his Horseman costume, skulks on the lawn behind them - and sees the real thing. He panics and runs.
Ian and Katie realize they have diverted the Horseman from original victim Ichabod Crane, to themselves. There’s only one thing to do.
They peddle back through the woods. As they near the Bridge of Souls, the Headless Horseman approaches. They shelter behind a bush. Katie insists on running out to distract the Horseman. While Ian runs to the Bridge, Katie weaves through the trees.
At the Bridge, Ian picks up Brad’s pumpkin, and taunts the sinister rider, who contemptuously catches the thrown pumpkin on his sword. Ian runs.
As Ian reaches the Bridge, the Horseman follows - and, in a whoosh of ethereal flame, dissolves.
Ian climbs up from beneath the Bridge. Behind, Ichabod has reappeared. He ponders to have taken a wrong turn, and decides to go right instead. With that, he rides off, and fades into the night.
In the distance, the Headless Horseman prepares to resume his annual pursuit...
Tucker brings the story to a close. One by one, the others pass with their verdict. Kiki decides he’ll do; an impressed Betty Anne gives Tucker a friendly high-five, and Frank wearily warns Gary to keep the kid out of his face. As the others walk off, Gary heartily welcomes his brother to the Midnight Society - whereupon Tucker runs to catch up with the others, leaving Gary to douse the fire.
This episode provides examples of:
- As You Know: Brad retells the Headless Horseman story despite Ian saying he knows it and Tucker already telling the whole story before beginning his own.
- Be Careful What You Wish For: So Sleepy Hollow is too "boring" for you, Ian...?
- The Bully: Brad tries to scare away Ian from his ex-girlfriend Katie with violence.
- Dead All Along: The man in eighteenth century clothes turns out not to be a costumed eccentric, but the ghost of Ichabod Crane.
- Deadpan Snarker: Ian.
- Endearingly Dorky: As noted by Tucker, Ian’s disarmingly awkward wit endears him to Katie and friends.
- Evil Laugh: The Horseman is accompanied by a disembodied bellowed laugh.
- Expy: The main characters' names — Ian, Katie, and Brad — start with the same letters as their counterparts' names in the original story (Ichabod, Katrina, and Brom).
- Friendly Ghost: Ichabod bids a friendly good evening, and politely requests directions.
- Ghost Amnesia: Ichabod doesn't seem to know that he's dead or that he's ridden this same route hundreds of times.
- "Groundhog Day" Loop: Each Halloween, the ghost of the Headless Horseman and that of victim Ichabod are said to resume their flight through the woods. However, on directing Ichabod to safety, Ian and Katie draw the Horseman to themselves.
- Headless Horseman: Naturally.
- Ironic Echo: Brad mocks Ian for screaming "Don't take my head!" when Brad successfully fooled him with his Headless Horseman costume. When the real Horseman starts charging towards him, Brad yells the same thing before stumbling away.
- Laser-Guided Karma: After Brad’s malicious prank, he continues to follow Ian around in costume, and gets the fright of his life when the real Horseman charges forth.
- Nothing Exciting Ever Happens Here: Ian's initial assessment of Sleepy Hollow? "Kinda boring." After the adventure's over? "And I thought this place was boring!"
- The Prankster: Brad sends Ian on an “initiation ritual,” to retrieve a pumpkin from the Bridge of Souls. He then jumps out, dressed as the Horseman; viciously mocks Ian's fright, and threatens him again for good measure.
- Real After All: For good measure, Brad is still in his Headless Horseman costume when the real deal shows up.
- Set Right What Once Went Wrong: Ian messes up the story by telling Ichabod which fork to take to get to the bridge. Katie concludes they have to set the story straight to get rid of the Horseman's ghost.
- Undeathly Pallor: Ichabod looks distinctly pale...
- Whole-Plot Reference:
- Subverted. While characters and events deliberately reflect those in The Legend of Sleepy Hollow, the episode serves as a belated sequel.
- Whether intentional or not, there are also parallels to Hocus Pocus in this episode: Boy moves into New England town famous for a local supernatural event from colonial times where he falls in love with a nice girl while incurring the wrath of the local bully before having the supernatural event return from the grave on Halloween night.
