Are You Afraid of the Dark Wiki
The Tale of the Midnight Ride
Season 3 , Episode 1
Air date January 8, 1994
Written by Darren Kotania
Directed by D.J. MacHale
Episode guide
The Tale of Old Man Corcoran
The Tale of Apartment 214

The Tale of the Midnight Ride is the First episode and season premiere of the Third season of Are You Afraid of the Dark?, as well as the Twenty-Seventh episode in total.


Midnight Society Cast[]

Story Cast[]


That evening, Gary seriously and sadly tells the group that friends come and friends go. Gary is sorry to say that now two members of "The Midnight Society," David and Kristen, have left because both of their families have moved away. They won't hear anymore stories from them, but they'll always be a part of The Midnight Society. Also they will be greatly missed and everyone looks sad after hearing that. Gary then tells them that there is now room for two new members. Gary asks Betty Ann if she knows anyone. Betty Ann mentions her friend Sam wants to join, but needs time to make an initiation story.

Gary has someone he wants to sponsor, so he brings in a short person with a burlap sack on his head. Kiki criticizes that person looks kind of small. The person pulls of the sack of his head and is revealed to be Tucker (Gary's little brother) and approaches Kiki and tells her, "I'll show you small!" Everyone is mad and annoyed to see a young kid there. Frank is really mad and annoyed and says, "Oh, come on, not your little brother," meaning that Tucker has possibly been a problem for sometime now. Gary tells them he has no choice; he either has to bring him or he can't come anymore.

Kiki can't believe what's happening and Frank says that they're not babysitters, and members have to tell stories. Tucker, annoyed by how belittling they are being to him, snaps and tells them if they would just lighten up then he could tell them a story. Gary then asks them to give him a chance, and Betty Ann responds with concern asking him if he doesn't bring his little brother would he'd really have to quit. Betty Ann, Kiki and Frank all reluctantly sit down. Gary shows Tucker to The Storyteller's chair but he sits on it instead and tells him his story better be a good one or Frank gets to pound him.

Tucker explains that people make up their own ghost stories all of the time. However, there are some ghost stories that have been around for so long that it makes you wonder maybe, just Maybe, it might not be made up. His story is about a famous ghost and a legend so popular, it just won't die. Tucker submits his story for the approval of The Midnight Society, calling his story "The Tale of the Midnight Ride."


Tucker tells the story, The story begins with a flashback to a battlefield during the American Revolutionary War. They called him the Headless Horseman. Legend says he was a soldier who had his head blown off by a cannonball. Night after night, his ghost would ride through the woods of Sleepy Hollow, searching for a victim to steal its head to it and claim it as his new one. Then one year on Hallowe'en night, the town's new schoolmaster Ichabod Crane took a wrong turn in the woods. He was then chased down by the evil horseman. Ichabod rode like crazy to get to The Bridge of Souls. This was the one bridge that the Headless Horseman could not cross. Poor Ichabod never made it on time and the Headless Horseman got him. Then Ichabod was never seen or heard from again. Legend has it that every since then on Hallowe'en night, the ghosts of the Headless Horseman and Ichabod Crane return to Sleepy Hollow to ride again.

Then the story resumes to modern time (when this first aired) at a high school in Sleepy Hollow. Students are seen leaving the school for the day. Now a young man politely opens the door for a girl to pass through. The young man is named Ian Matthews. He had just recently moved to Sleepy Hollow and was trying hard to make friends and fit in. It was like everything he did sometimes he tried a little too hard. A pretty young girl is seen walking up to the school carrying a box of Hallowe'en decorations. Then unexpectedly, another young man named Brad (who is Katie's jealous and possessive Ex-Boyfriend) throws a ball at her. This knocks the decorations out of her hand spilling them on the ground and she snaps at him feeling annoyed.

Ian goes over and politely helps her pick up the decorations. Then she says that Brad really makes her mad at times. Ian introduces himself and she introduces herself as Katie realizing they're in one of the same classes together. Katie explains the decorations are for the Hallowe'en Dance that night, and he politely offers to help her set up. Katie really appreciates the help, and she is annoyed when she realizes that Brad accidentally crushed one of the pumpkin decorations. Brad stops on by and says he was going to help. Ian rudely snaps at him and tells him to fix the decoration right away because they're setting up the dance and they both storm off to the school. Brad is not too happy to see Katie being friends with Ian. Then his friend remarks about him possibly putting moves on her and Brad tells him not if he wants to live.

Inside the school, various students are setting up all sorts of creepy and spooky Hallowe'en decorations. Ian is standing on a ladder while stapling Jack O'Lanterns to the ceiling. Katie asks him how he likes Sleepy Hollow so far. Ian tells her it is nice, but a little boring. Because he came from the city and has only been here since the past summer. Brad rudely comes by and addressing her as "Babe" and asks her if she wants any help. Annoyed, she tells him no "Babe" and they are almost done. He then much to her annoyance puts his arm around her. Now he asks her if she going to the dance with him.

She shakes him off and tells him that it's over. They don't go out anymore and she is fed up of reminding him. He rudely tells her that he'll say when they don't go out anymore. Then Ian accidentally drops a decoration on his head. Brad is mad, thinking he might have done it on purpose. So he pulls the ladder away from his feet leaving him dangling from the ceiling. Brad threatens Ian and telling him to stay away from her unless he wants to walk around toothless and he storms off. Katie comes back and brings the ladder back to help get done. She apologizes for how much of a jerk he can be. Feeling scared, Ian says also he can be scary too. Katie tells him to not let him bother him. She then asks him to save a dance for her when they're at the dance that night.

Ian arrives to the dance by his bicycle. The school dance is a real success and everyone is having a wonderful time. Katie happily meets Ian at the dance, and they coincidentally are wearing either Victorian era or Colonial era costumes with three pointer hats. She remarks about how they're like twins and he says that great minds think alike. Ian gets a little nervous when they see Brad rudely walking by dressed like a pirate. They don't let it bother them and they head off and dance with each other. After some time that night, Ian is hitting it off with Katie and some more classmates. They think he's very likable and funny and they enjoy his company. That is everyone except for Brad, Ian didn't know it at the time. But he was walking through some very dangerous territory. After another dance with a classmate, he notices Brad harassing and annoying Katie again. Brad is making her feel exasperated and wanting to leave. Ian tries to intervene asking how they are doing, but Brad rudely pushes him away calling him a geek. He stands up for her and tells Brad that he doesn't think she wants to talk to him and that he should leave her alone. Brad gets really mad and tries to fight him, which Katie breaks up.

Outside the school, Brad is standing with his friends and Ian and Katie are standing on the opposite side. Ian has fists up and is ready to fight him. Brad asks him to put them down because he doesn't want to fight him. Instead he wants to do him a favor. He tells Ian the legend of Sleepy Hollow, how back in the late 1700's on Hallowe'en night, Ichabod Crane got lost finding his way home. Ichabod should have gone left, but he went right instead. Instead of getting to The Bridge of Souls, which was the one bridge the Headless Horseman could never cross, he went deeper into the woods.

Ian interrupts Brad claiming that he knows the rest of the story. How the Headless Horseman threw a pumpkin at him and took his head and says it is just a story. Brad tells him well it's Hallowe'en and they have a tradition in Sleepy Hollow. When someone new shows up they need to be initiated. Katie tells Brad to give it a rest and Ian mockingly asks if he is going to take his head. Brad tells him no, because the bridge is still there and he has to cross the bridge and bring back the Headless Horseman's pumpkin just like everyone else did. Brads tells him either he goes and gets the pumpkin and they'll leave him alone. Or he and Ian will fight after all. Ian says he doesn't believe in ghosts so he'll get the pumpkin. Katie tells him he doesn't have to do it. But he wants to prove himself to everyone and goes off to find the pumpkin.

Ian heads off into the dark bushes of the nearby woods. He walks along and heads down a path holding a flashlight. He nervously whistles while checking his every move, as he goes further into the dark foggy woods. Soon he finds the bridge and finally the pumpkin. He is a bit startled at first to see it's a Jack O'lantern gleaming a green aura. Then he opens it to find a green glow stick inside. He realizes it was just Brad and his friends prank. Then in the distance he can hear loud evil laughter, "Ha-ha-ha-ha." Ian shouts that he knows it's Brad and to give it rest. Then he is about to call out for them to give him a break.

Then suddenly what appears to be the Headless Horseman! He is standing on the bridge wielding a cutlass sword. He chases Ian all the way back as Ian is screaming and crying for help. He falls down on the ground and is huddling begging for him not to take his head. Then suddenly the Headless Horseman says, "BOO!" It lifts off the robes it is revealed to be Brad in disguise and Brad and all his friends are laughing at Ian. Katie helps him up and checks if he is all right. Brad threatens Ian not to mess with him. Then he asks Katie to leave with them. She chooses to stay with Ian, because she is fed up with Brad and his bullying antics and she asks them to leave them alone. Brad leaves them alone warning them that it's Hallowe'en night and the real Headless Horseman is out there. Then he claims that Ian definitely doesn't have the guts to stand up to him.

Ian happily agrees to walk Katie home. Just as they leave, in the woods the Headless Horseman can be seen and heard. Ian and Katie are walking closer back when they suddenly hear a horse neighing. They look around to see a man dressed in white clothes with a three pointer hat, riding a white horse. He is very polite and friendly. Then he apologizes for startling them, and tells them he has lost his way and if they could lead him to The Bridge of Souls. Ian tells him to take the left turn. Then the man thanks him really appreciating the help. He says that without it he certainly would have gone the right way. He thanks them and rides off. That is just when they find out he is none other than Ichabod Crane.

Ian finally walks Katie back to her home, they tell each other they're really happy they met each other and would really like to see each other again. Ian is about to give Katie a goodnight kiss when her porch light goes on. To avoid being caught by one of her parents, he tells her he needs to head back to the school because he forget his bike there. On Ian's way out, he hears the neighing of a horse again. He thinks he is just hearing things and shakes it off. He then hears the footsteps of horse hooves and on the foggy bridge, a horse man can be seen who laughs sinisterly. Ian runs off to the school about to get his bike. Then he can hear the distant presence of the horseman. Thinking it is Brad again, he calls out for him to leave him alone and to give it a rest. Ian is about to unlock his bike when he remembers the key is in his coat which he let Katie wear home to stay warm.

He turns around and is startled to see Katie there. She rode over on her bike to return to him his jacket and his keys. They prepare to ride back home when suddenly Katie gets nervous and points out the shadow of a horseman cast up the wall of the side of the school. Thinking it is Brad not giving up, he walks closer to it. He shouts out to Brad. He tells him to leave Katie alone because their relationship is over and she doesn't like him anymore. Also if he wants to fight, then they will fight.

The shadow appears on a wall again and diabolical laughter is heard. Then the real Headless Horseman emerges from the walls shadow and rides up to him. He swings his cutlass at him which Ian dodges in the nick of time. He runs to Katie and points out the Headless Horseman is for real and that the story is now true. the Headless Horseman drops his pumpkin and begins to chase the both of them as they head of on their bikes. Brad, on his way out from the dance, can see it too. Now he screams not to have his head taken.

Katie and Ian hide along the side of the wall and she wonders why the Headless Horseman is after them instead of Ichabod. Ian says it was because they accidentally helped Ichabod and gave him the correct direction. Therefore, he never became the victim, and they changed the story.

Katie says they have to play the story out and cross The Bridge of Souls. Then they get closer and closer and riding their bikes at full speed. They are literally riding for their lives as the Headless Horseman keeps getting closer and closer. They just miss him and hide in some bushes. Katie plans to distract him while Ian leads him to just where the bridge is. Katie distracts him by hiding between the trees, and he is about to decapitate her when Ian picks up the pumpkin and calls out that it's him he's after. Thinking the story works both ways, he tries throwing the pumpkin at the Headless Horseman, but nothing happens he just catches it.

Katie screams for him to run for the bridge. Ian runs for it at full speed with the Horseman right behind him. Ian makes it and the Headless Horseman turns into flames and bursts away and vanishes. Katie calls for Ian and there is no answer. Then he comes up between the fence, seems he either fell down or jumped over when The Horseman came. Katie is rejoiced because the story was set straight again.

Ichabod returns and lectures them for being out so late on Hallowe'en night and in the woods that are said to be haunted. Ichabod claims he came back because he lost his way again. This time he thinks he should take the right turn after all, which should set things straight. Katie agrees with Ichabod's decision. Ichabod leaves them telling them to take care and beware the Headless Horseman and wishes them a Happy Hallowe'en. After Ichabod has left, in the clearing of another part of the woods, the Headless Horseman is shown to be all right and laughs and rides off into the night.


As Tucker ends his story, Gary stands up and asks the other three what they think of his story. Kiki pats him on the shoulder and tells him, "You'll do." Betty Ann smiles at him and does a handshake with him and tells him, "Excellent." Frank tells Gary, "Just keep him out of my face." Tucker, in victory, says, "Yes!" knowing he earned most their respect and Gary welcomes him to the group and they half five with each other, Tucker tells Gary to put out the fire as he going to catch up leaving with the others. A bit annoyed, Gary puts out the fire and says that he hopes he doesn't regret letting him join.

  • This episode introduced a new member of The Midnight Society: Gary's little brother, Tucker (Daniel DeSantos).
  • Tucker's first story.
  • As stated by his official Collector Photo Card, this story is Tucker's favorite.
  • At the beginning of the episode, Gary announces that Kristen and David's families have moved away. According to an interview with D.J. Machale, Nathaniel Moreau (David) was terminated due to salary disputes and Rachel Blanchard (Kristen) personally called him and said that she simply didn't want to do the show anymore.
  • After this episode David and Kristen were never mentioned again.
  • This is the only episode where an actual location was known for the story setting (Sleepy Hollow, New York).
  • Brad's character might have been based on the character of Brom Bones.
  • Katie's character might have been based on the character of Katrina Van Tassel.
  • Arthur Holden who portrayed Ichabod Crane, Appeared again in the series 2 more times. The second he portrayed Mr. Brooks in "The Tale of the Dead Man's Float". The third time he portrayed The Court Jester in "The Tale of the Wisdom Glass", in the series revival.
  • Arthur Holden co-stars with Jodie Resther in the Children's program Arthur as the voice of Mr. Ratburn.
  • Daniel DeSanto co-stared with Rachel Wilson in the TV show Total Drama. He did the voice of Dave, she did the voice of Heather.
  • Daniel DeSanto has said that this is his favorite episode.