It was the night after Nightmare Night and everything was quiet. It was bright because there is a full moon and has been empty since Luna was released from her banishment. The mane six were in Twilight's room, listening to a story.

"And so, the little filly managed to get out of the haunted house just in time before it collapses to the ground. All she did was running away from this place and never coming back. She never talked about it since." Twilight read. "Pretty spooky story, huh?"

"I don't know. It didn't have much detail to it. All she did was going inside a haunted house and then it collapsed just like that. What kind of a house haunted is that anyway? I mean, I didn't have ghosts or zombies living in that house." said Rainbow Dash. "I think it's scary. Because if the filly is scared, I'm scared." said Fluttershy. "Is there another scary story for us? Something that'll be much more scarier." Pinkie asked.

...

While they're talking, the Book of Disney is calling them.

"Hey, maybe the Book of Disney will give us a scary story." said Applejack. "Let's see." said Twilight as she and her friends went to the throne room.

When they got there, Twilight opened the next chapter. The next story is The Legend of Sleepy Hollow. She began to read,

"This is a dark tale about Ichabod Crane who comes to a town named Tarry Town and is a teacher. He loves food and never gets fat. While he's there, he falls in love with the daughter of a wealthy rich man. Her name was Katrina Van Telsing. She wins the hearts of many men in the village, but the man who wants her was the towns hero Brom Bones. Everyone loves him because of his good skills and is caring to everyone. But, he's not very caring to Ichabod since he has feelings for Katrina. What you should know is the Headless Horseman. He's the ghost everyone fears and comes out every night, looking for a new head."

Once Twilight is done reading, she and her friends get sucked into the book.

...

The mane six ended up in a village called Tarry Town.

"Where are we?" Rarity asked. "I thought we were supposed to be in a scary story." Rainbow Dash complained. "We are. It's just that it gets haunted during the night. It's daytime now." said Twilight. "Do you think we should find Ichabod Crane first?" Applejack asked. "You're right. I think he just moved here to become the new teacher for the town." said Twilight.

So, the girls entered the town and sees its very busy. That's because all of the men are paying attention to Katrina who is walking through town. "Is that Katrina?" Fluttershy asked. "I think so. Let's ask her." said Applejack.

They went up to her to ask her questions. "Excuse me. Are you Katrina Van Telsing?" Twilight asked. Katrina turned around and said, "Yes, I am. How can I help you girls?" "We're looking for a new guy named Ichabod Crane. Have you seen him?" Rainbow Dash asked. "And did you know he has a huge crush on you?" Pinkie asked. Katrina giggled and said, "Well, he's over there giving girls music lessons. He's one heck of a ladies man, if you ask me." "Great. Thank you." said Twilight.

"Oh, girls. One more thing. I want to invite you to my father's halloween party." Katrina called. "A Halloween party!? Oh boy! Oh boy! Let's go!" Pinkie shouted. "Are you going to invite Ichabod?" Twilight asked. "I'm inviting everyone in the town, including Ichabod. The party's tomorrow night." Katrina answered. "Ok. Thanks for the tip." said Twilight as she and her friends left to find Ichabod.

"A Halloween party. Wouldn't that be fun?" Pinkie asked. "It sure will. Besides, it'll help Ichabod get to know Katrina and falling in love with her." said Twilight. "But, what about Brom Bones? He has a crush on Katrina too." Rainbow Dash warned. "You're right. We should aware of that. I have a feeling Katrina invited him to the party." said Twilight. "So, what can we do about it?" Applejack asked. "We'll see. Perhaps we should wait when the party starts." said Twilight.

They found Ichabod playing the piano with three women.

...

He couldn't hear the mane six coming in because the piano is too loud for him to hear everything else around him.

"Ichabod! Ichabod Crane! Excuse me!" Twilight yelled. Ichabod can't hear her. "ICHABOD CRANE!" Rainbow Dash yelled. Ichabod finally heard her and stopped playing his piano. He turned around and asked, "Why, hello there. How may I help you lovely ladies?"

"Ichabod, we came here to help you win the heart of Katrina Van Telsing." Twilight explained. "You do? Ahh, the lovely Katrina. Wish I can have her hand in marrige. But, that Brom Bones wanted her too. I just don't know what to do." said Ichabod. "Well, that's why theres this Halloween party you're invited to tomorrow night. Maybe you can win her heart there." said Rarity. That cheered him up. "Say, that's it. Thanks, girls. But, I don't know your names." he said.

"I'm Twilight Sparkle and these are my friends. Pinkie Pie, Applejack, Fluttershy, Rarity, and Rainbow Dash." Twilight introduced. "Pleasure to meet you. So, when can we plan on what we should do at the party?" Ichabod asked.

"Why don't we do it now?" Twilight asked.

...

The next day, the mane six and Ichabod are getting ready for the Halloween party.

Ichabod was dressed in his best suit and his hair is nice and straight. Rarity is making dresses and hairstyles for herself and her friends. She also puts makeup on just to look good.

"Ok, girls. We are ready to go. You nervous, Ichabod?" said Twilight. "Nope. I'm ready to see the girl of my dreams. Wish me luck." Ichabod replied.

Ichabod borrowed a horse from a nearby farm and they're off to the Halloween party.

...

There, they danced through the music while Pinkie is busy eating pumpkin pies.

Ichabod is having a great time since he gets to dance with Katrina throughout the entire party. Twilight and her freinds watch while dancing. "Isn't that romantic? Who knew we are so good with romance." said Rarity.

While dancing, Applejack saw Brom Bones sitting in the corner pouting. Probably he's jealous of Ichabod dancing with Katrina. "There's Brom Bones like you said." she said to Twilight. She sees him as well and said, "Well, I think we need some distraction so he won't get to Katrina." "How do we do that?" Applejack asked. "A girl that can dance with him and I know just the pony." said Twilight, looking at Applejack in a sneaky smile. "Uh, Twilight. Why are you looking at me like that?" Applejack asked in a nervous way.

Twilight pushed her close to Brom so he can see her. Applejack gulped at this. "Howdy there, partner. Sure is nice of you to come to the party. I'm Applejack." she said nervously. Brom looked at her and said, "Are you a pony dressed as a towns girl?" "Yes. Look, my friend made me dance with you. So, just shut up and dance with me!" Applejack yelled. "Okay then." said Brom as he began to dance with her.

He twirls her around and lifts her in the air. Applejack screamed the entire time. "Twilight!" she yelled. Twilight just watched and winked at her.

...

After the dancing, everyone gathered around to talk to each other. Applejack was pretty mad at Twilight for making her dance with Brom.

"I can't belive you forced me into that. Would've been nicer if you made Rarity do it. She would've had a good time." said Applejack. "Sorry, Applejack. I have to, so Katrina won't be taken away from Ichabod." Twilight explained. "Ok, I forgive ya, but don't make me dance with anyone ever again!" Applejack yelled. "I won't. I promise." Twilight promised.

Pinkie was eating food with Ichabod like pies and cupcakes. "Let me tell you, this pumpkin pie is delicious." she said. "I'll say. Wait till you eat the rest of the food." said Ichabod as he eats a stick of celery.

Brom Bones appeared in the center near the fire place, calling out, "Hey everyone! Listen up! I have something to tell you. Something that'll make you scared of the dark." Rainbow Dash disgusted at this and muttered, "Nonsense. Nothing scares me." "What's that you say? Nothing scares you? Well, this tale will. A tale of the Headless Horseman." Brom said. "Is he real for fake?" Fluttershy asked. "Oh, he's real alright. Just listen to this tale." said Brom.

Then, he begins to sing,

(When spooks have a midnight jamboree,
they break it up with fiendish glee.
Now, ghosts are bad,
but the one that's cursed
is the Headless Horseman,
he's the worst.

That's right,
he's a fright on Halloween night.

When he goes a-joggin'
cross the land,
holdin' his noggin',
in his hand,
demons take one look, and groan,
and hit the road for parts unknown.

Beware, take care, he rides alone.

Now, there's no spook like the spook who's spurned.

They don't like him, and he's really burned.

He swears to the longest day he's dead,

he'll show them that he can get ahead

Now, they say he's tired of his flamin' top,
and he's got a yen to make a swap.
And so he rides one night each year,
to find a head in Hollow here.

Now, he likes them little, he likes them big.

Part in the middle, or a wig.

Black or white, or even red.

The Headless Horseman needs a head.

With a hip-hip and a clippety clop,
he's out looking for a top to chop.

So don't stop to figure out a plan,

you can't reason with a headless man.

Now, if you doubt this tale is so,
I met that spook just a year ago.
Now, I didn't stop for a second look,
but headed for the bridge that spans the brook.
For, once you cross that bridge, my friend.

The ghost is through, his power ends.

So, when you're riding home tonight,
make for the bridge with all your might.
He'll be down in the Hollow there.
He needs your head.
Look out! Beware!

With a hip-hip and a clippety clop,

He's out looking for a head to swap.

So, don't try to figure out a plan,
you can't reason with a HEADLESS MAN!)

When he's done singing, Ichabod was shaking all over the place. Katrina just laughed because she likes it when he gets scared. As for the mane six, Pinkie and Fluttershy were frightened by the story. Rainbow Dash wasn't scared of the story at all because she thought the Headless Horseman is a made up story.

"This isn't scary. It's just a plain old myth." she said.

...

As they walk through the forest after the Halloween party is over, Ichabod tried to calm himself down from the story Brom told him by whistling to himself.

"Rainbow Dash. Do you think the Headless Horseman is real?" Fluttershy asked. "Please. The Headless Horseman is not real. Brom made it up just to scare us." Rainbow Dash answered. "You sure about that, Rainbow Dash? The Book of Disney did warn us that the Headless Horseman comes here every Halloween night and tonight is Halloween night." said Twilight. "I'm sure he's fake." said Rainbow Dash.

Suddenly, they hear some hooting coming from an owl which scares Ichabod. "What? It's just an owl." said Applejack. "That scared me too. Come on, we better get outta here quickly." said Rarity. "You're right. This forest is creepy at night. Let's just keep going." said Twilight.

Then, they hear a croaking voice calling Ichabod's name. "What was that?" Fluttershy asked. "I don't know. This is creeping me out." said Pinkie. "I don't know what it is, but I'll find out! said Rainbow Dash as she pushed some leaves out of the way and the sound came from a frog that's just croaking. "False alarm guys. It's just a frog croaking." she said.

Everyone sighed in relief. "That was close." said Pinkie.

Then, they hear some clopping noise, sounding like horse steps. Ichabod shouted and hides underneath his horse. "ITS THE HEADLESS HORSEMAN!" Pinkie yelled as she hides behind Twilight. Twilight readies her magic to zap whoever is frightening her friends.

Once she did, it is revealed to be cattail plants hitting on a log. "See? I told you the Headless Horseman is not real!" said Rainbow Dash. They sighed in relief once again. "I guess you're right, Rainbow Dash. There is no such thing as the..." said Twilights, but got interrupted by an evil laugh. This startles the mane six and Ichabod.

The evil laugh came from none other than the Headless Horseman.

The mane six and Ichabod screamed in terror and immediately ran for their lives. "I guess you were wrong about the Headless Horseman being a myth!" Applejack yelled as she ran. "I know! I'm so sorry!" Rainbow Dash yelled as she runs with her friend. Twilight zapped the Headless Horseman with her magic, but he got over it and still chases them. "Uh oh. Not good." she said.

The Headless Horseman laughed as he swung his sword at Ichabod, but misses. Rainbow Dash kicks him on the shoulder, but nothing worked. "What do we do now? He's too invincible to fight!" Rarity yelled. "We need to find his weakness! It's the only way to defeat him!" Twilight yelled back. "But, he doesn't have a weakness!" Fluttershy cried out.

They keep running until they reached the bridge nearby. "We have to cross the bridge! Maybe that'll be his weakness." said Twilight as she and her friends crossed the bridge safe and sound. They were all panting as they got away from the Headless Horseman. "So, that bridge is his weakness. Strange, but good." said Rarity. "Shouldn't he be leaving?" Pinkie asked as she sees the Headless Horseman still standing there with his horse. Twilight looked at him and said, "I don't know. Come on, we should get back."

But before they can do anything, the Headless Horseman has a flaming pumpkin in his hand and throws it at Ichabod. Ichabod screamed in terror as the pumpkin was thrown at him. The girls tried to save him, but it was too late. Ichabod was gone.

Then, the girls disappeared after the tragedy happened.

"ICHABOD!" Rainbow Dash yelled in fear.

...

The Book of Disney sent the girls back home.

Rainbow Dash immediately went to the book and opened it to see what happened to Ichabod. "Ichabod! Ichabod!" she cried out. Twilight went to her and said, "Rainbow Dash, it's okay." "No, it's not okay. It's all my fault. I'm the one who didn't believe in the Headless Horseman. And then, he just killed him. I can't believe it." Rainbow Dash cried. Twilight hugged her to comfort her.

"There there, Rainbow Dash. You'll be okay. I'm here." she said. Rainbow Dash's eyes were filled with tears.

...

That night, Rainbow Dash began writing in the Disney Journal. She wrote,

"What I learned today is about believing. I didn't believe in the Headless Horseman because I thought he was just a myth story for Halloween. Now, I learned he's real and nothing can stop him. If you don't believe in a story, go see for yourself if it's real or not."