JONATHAN: Hello, my spook-tacular dork squad, and Happy Halloween! Many of you will be gearing up for your Halloween festivities—putting on your costumes, lighting your jack-o’-lanterns, and maybe even getting ready to collect a mountain of candy. And for those of you who do not celebrate Halloween, you’ll still enjoy this spooky—but not *too* spooky—story Redge and I told you in Season 2 of our show.
Today’s tale is inspired by the classic Legend of Sleepy Hollow, a story written way back in 1819 by Washington Irving. It’s all about a small, quiet town with some big, mysterious legends, including one very famous ghost—the Headless Horseman! But don’t worry, our version is full of funny moments and, it sets the perfect eerie mood for your Halloween night.
So grab your candy, turn off the lights, and get ready for our encore presentation of *Sleepy Hallow’s Eve*—a tale that will give you just the right amount of shivers and giggles!
JONATHAN: JONATHAN CORMUR: Hello Dork Squad. I'm Jonathan Cormur and you're listening to Dorktales Storytime, the podcast for kids and their pop culture-loving grown-ups.
THEME SONG: It's a beautiful day for a story, adventure and glory, new friends and old ones too. It's an excellent day to get swept away in a tail, so let us regale you.
Spooky sfx and creepy organ music.
JONATHAN: Oh hello boils, ghouls, and non-corporeal entities! It is me! The Cr---”coughs chokes hacks* (returns to normal voice) The Narrator! (returning to Crypt-Keeper-esque theatricality) Or for this story’s purposes… the SCARE-rator! Muahahahaha!
REDGE: Hold on. The Scare-rator?! What is going on here, Jonathan?! I only asked-
JONATHAN: -You only asked if I would help you get into the spirit of Halloween before you head out to trick-or-treat! Right, Redge?
REDGE: Wel...erm...yes, but-
JONATHAN: And that’s exactly what I’m doing! I’m here to SCARE-arate a spooky tale that’ll make your quills stand on end!
REDGE: My quills always stand on end. Why are you using that ridiculous voice?! AND what is with this robe and beard just to hand out candy? Why are you dressed as Dumbledore?
JONATHAN: Well, to be honest, I’ve eaten most of the candy and “Dumble” is one “door” I won’t open! But I’ll definitely give you a hint about my character...ahem, “YOU SHALL NOT PASS!”
REDGE: Pass what? Gas? Too late chap, that’s the first treat I’ve tricked today…
JONATHAN: Oh poor, young, totally vulnerable, Reginald! You may be flippant about my costume as GANDALF, one of the greatest wizards of all time, but what’s truly frightening is that you’re also forgetting the point of this spooky holiday....
REDGE: The point? To trick sweets from the gullible fools who think I’m actually Sonic the Hedgehog!
JONATHAN: Hate to break it to you, buddy, but you can’t just paint your body blue and trick people into thinking you’re Sonic.
REDGE: I could if I didn’t leave my many golden rings at home!
JONATHAN: The only thing you’ve left is tiny blue footprints all over my carpet...why would you paint the bottom of your feet?! ?
REDGE: Commitment! Besides, didn’t you learn how to magically clean up paint at Hogwarts?!
JONATHAN: I’M NOT DUMBLEDORE! FOR THE LAST TIME, I’M GANDALF THE GREY FROM LORD OF THE RINGS!
REDGE: Whoa, Jonathan. I was just having a little fun...you’re getting kind of scary.
JONATHAN: I am?
REDGE: Yes, I only came here for treats before meeting up with Thomas the Turtle and the Loppy sisters, Flippy and Floppy…
JONATHAN: Well there’s lots more to Halloween than just trick-or-treating, Redge. Sometimes people LIKE to feel the exhilaration of fear. In fact, people often go out of their way on Halloween to be scared…
REDGE: Like how?
JONATHAN: By telling scary stories. Are YOU ready for one?
REDGE: Well apparently I haven’t been celebrating Halloween fully, so why not? But I have to warn you, I don’t think I can be scared.
JONATHAN: Are you sure about that?
REDGE: (a little timid) ...no...um...yes?
JONATHAN: (in Crypt Keeper voice) GOOD! Let me tell you a tale that will send shivers up your quivers and make your teeth chatter from fright. This is the Legend of Sleepy Hollow...or as some like to call it, the story of the headless horseman!
REDGE: Oooh. I just shivered. Felt like an ice cube ran down my spine.
JONATHAN: Once upon a time, in the town of Sleepy Hollow...
REDGE: (yawns) You said this story was scary, not sleepy...just the name is making me tired. Don’t know how I’ll go trick or treating now…
JONATHAN: Don’t judge a story by its title! This one’ll definitely wake you up. Once upon a time, in the town of Sleepy Hollow lived a kindhearted schoolteacher named Ichabod Crane.
REDGE: Ichab-”odd” is right! What a peculiar name!
JONATHAN: Well that’s not all, in Sleepy Hollow, there were other interesting characters. like Brom Bones and Katrina Van Tassel!
REDGE: Oooh Brom Bones sounds like an interesting character...was he quite...HUMERUS?!
JONATHAN: Ha! Good bone reference buddy, now you’re getting it.
Now, ...back to Sleepy Hollow…
REDGE: None of this sounds very scary yet, Jonathan.
JONATHAN:(Crypt Keeper voice) Just you wait! Muahahahaha!
REDGE: Fine. But no more scare-arator voice.
JONATHAN: No promises... where was I? Oh yeah, Brom Bones. Brom was a pretty well-known young dude about town. He had always been the largest and strongest kid, and he grew into the loudest and strongest young man with a large ego to boot. He was VERY sure of himself.
REDGE: Sounds a little too sure, if you ask me.
JONATHAN: You’re absolutely right. Brom was a bit of a bully. And you know who he loved to pester?
REDGE: Must be the odd one. Ichabod.
JONATHAN: Exactly! Ichabod was sweet and smart, but not large and strong enough to stand up to Brom’s bullying. Brom would often corner him in the market, and yell out loud enough for everyone to hear:
BROM: Oh it’s ol’ ick-a-dee-doo-da. Mr. Icky-picky-sticky-tricky-bod Crane. Are you lost or something?
REDGE: Ruthless.
JONATHAN: He truly was. Some say Brom was just out to get Ichabod because he was unhappy with himself, others just think Brom liked to see Ichabod squirm under his menacing glare, but regardless of their theories, everyone agreed that tension between Brom and Ichabod got much, much worse when Katrina Van Tassel came into town…
REDGE: Ooh I had forgotten about her! How did I miss that?
JONATHAN: You were too busy making fun of the names Brom Bones and Ichabod Crane.
REDGE: Well I’m just trying to liven it up a bit.
JONATHAN: How about we DEADEN it up a bit.
REDGE: Are their zombies?
JONATHAN: Well...not really, no.
REDGE: Then what are you going on about Jonathan? This story won’t scare me!
JONATHAN: We haven’t come to the chilling and creepy part of the story yet! Katrina Van Tassel was a very beautiful young woman and both Brom and Ichabod were smitten with her. In fact, the second Ichabod laid eyes on her, he said to himself:
ICHABOD: That w-w-woman will be my wife!
REDGE: Bold, confident statement!
JONATHAN: It was! But remember he only said it to himself.. See, Ichabod had a lot of superstitions—wouldn’t walk under ladders, avoided whistling, even steered clear of mirrors for fear of accidentally breaking one and ending up with seven years of bad luck. They were rituals that kept Ichabod feeling safe!
REDGE: I see!
JONATHAN: He was a good schoolteacher and a soft-spoken person, so he rarely spoke his feelings out loud. And to make matters worse, when he followed Katrina Von Tassel around...he became even more nervousl...and who likes to pick on the nervous guy?
REDGE: Uh oh...the big bully.
JONATHAN: Right again! One day, Brom spied Ichabod trailing behind Katrina in the bookstore Icabod’s father owned.
KATRINA: Here, hold these as I browse a bit more.
JONATHAN: Katrina was guiding around the dutiful Ichabod as she perused the shop. Suddenly, from behind a stack came broad-shouldered Brom standing at the ready to intimidate the small, book-laden Ichabod.
BROM: Ho ho! What have we here!
JONATHAN: Thundered Brom.
BROM: Lil Icky must be tripping all over himself to have the chance to be near a flower such as you!
JONATHAN: He took Katrina’s hand and feigned concern.
BROM: I’m so sorry, fair Katrina, for this slobbering fool...did he get any of his drool on you?
JONATHAN: Meanwhile Ichabod was feeling a bit more sure of himself as he gathered the courage to speak.
ICHABOD: BROM!
JONATHAN: He finally burst out, as if by accident.
ICHABOD: You’ve never even tried to get to know me! You’ve unfairly judged me and you’re acting like a mean-spirited bully!
JONATHAN: A hush fell over the bookstore as Ichabod’s jab sank in.
BROM: What did you say to me , lil Icky?!
JONATHAN: Asked the smouldering Brom. Ichabod squared his shoulders up to face Brom confidently.
REDGE: Yes! Go oddball!
JONATHAN: Ichabod. And he replied:
ICHABOD: I’m going to tell you just once to leave this shop before my father and I kick you out!
JONATHAN: It was an empowered move by Ichabod. He must’ve felt confident because he was on safe ground in the shop. And after Brom stormed angrily away, Icahbod’s father came around to make sure everything was alright, and Katrina extended an invitation.
FATHER: Ho! I’ve never seen Ichabod so firm and animated! You’re a good influence, Miss Van Tassel!
KATRINA: Oh it was very special to see him stand up for me! You should come to my Halloween party tonight, Ichabod! Everyone from town will be there!
JONATHAN: Ichabod was on cloud nine having stood up to his bully and in front of his father and the woman he loved! And on top of that, an invitation to the Van Tassel family’s Halloween party? What could go wrong?
REDGE: Oh is this one of those breaded fish moments?
JONATHAN: What? That’s not scary.
REDGE: No, but it’s a breaded fish. You know the moment in a story that leads the listener to believe something untrue?
JONATHAN: Ohhhhh...you mean a “Red Herring”?
REDGE: Yes! Breaded fish, red herring, same thing! What’s with all these silly names? Ichabod Crane...Brom Bones! Red herring?!
JONATHAN: Well yes I guess “what could go wrong” was a little misleading...but you know this is a (Crypt Keeper voice) spoooooky story.. things WILL go wrong.
REDGE: Your creepy narration and the anticipation is starting to get to me! I’m at full attention now! What happened at the party?
JONATHAN: Well, sure as Katrina predicted, everyone from town was there. Sporty Brom, and skittish Ichabod were both vying for her attention all night. Each of them kept bringing her canapes and refilling her cup whenever it was empty. It was overwhelming. But, even to his own surprise, Ichabod’s sweetness was clearly charming Katrina more than Brom’s overly confident attempts. Ichabod and Katrina laughed and danced together almost all evening.
REDGE: Can’t be good.
JONATHAN: Right. But Brom was saving a secret weapon of his own. See, Brom knew Ichabod’s gentle demeanor easily gave way to superstition and fear...and Brom was going to take advantage of it. So during a break in the dancing and music, Brom called all the partygoers over and told them a story...one he knew that would make Ichabod squirm and shriek, especially in front of Katrina.
REDGE: What? No story can do all that!
JONATHAN: This one can! Brom told of a ghost horseman who rides through the hills surrounding their town, seeking new victims to chase. And he always finds them...even though he has no head!
REDGE: Oh that’s not too scary! Some people think I have no head, but it’s just because it’s the same width as my body. What I truly have...is no neck.
JONATHAN: Well that story may not have frightened you, Redge, but it definitely did a number on Ichabod Crane.
REDGE: Poor Ichabod.
JONATHAN: Yep. After the story was told, Ichabod didn’t feel like having anymore Halloween party fun. His hands trembled, so he stopped refreshing Katrina’s cup after accidentally spilling punch on, not one, but three women’s dresses. The night was turning into a failure, and superstitious Ichabod took it as a sign to head home. He thanked Katrina for hosting, and left just before midnight.
REDGE: Oooh! I heard that time’s commonly called “the witching hour!” (thunder sound)
JONATHAN: What a great tidbit of information. Yes, Ichabod Crane left the party at the witching hour ( repeat thunder sound) and made his way home, but his house was on the other side of town. Instead of winding through the streets, he knew it was faster to pick up his trusty horse “Powder” from the corral and ride home on a straight path in the woods. Though the path seemed a bit different that night…
REDGE: Different how? Like how you think Dumbledore and Gandalf are different? Even though it’s the same costume?
JONATHAN: It’s not the same costume! Whatever. Anyway Ichabod spoke to himself as he made his way across the field to the corral. It was a path he knew well, but somehow…
ICHABOD: W-w-w-wow. I g-g-guess the m-m-m-moonlight makes this field look a bit l-l-larger...and the music coming from the party is d-d-d-distorted… kind of sp-sp-sp-spooky.
JONATHAN: He spoke aloud to himself to cut through the fear, though his lips were quivering and he hadn’t yet reached where he had tethered Powder.
REDGE: And another thing!
JONATHAN: Oh boy.
REDGE: Why is it taking him so long to cross the field?
JONATHAN: He’s scared! Inching his way down the path seems like it takes a LOT longer when you are nervous.
REDGE: Then why wasn’t he called “Inch-abod Crane”?! AHAHAHA
JONATHAN: (over it) Are you ready for the rest of the story now?
REDGE: Well you’re inching along…
JONATHAN: Ok fine. Incha-bod…I mean, Ichabod hopped on Powder
REDGE: Was he a white horse?
JONATHAN: Powder can be grey! Powder can be black or chestnut brown! There are lots of types of powder!
REDGE: Didn’t mean to strike a nerve there.
JONATHAN: Well we’re getting to the exciting part of the story…
REDGE: Alright I’m done interrupting… ready to be frightened.
JONATHAN: So Ichabod and Powder were making their way through the shortcut in the forest when they started hearing a thump thump thump behind them…
REDGE: Oh goodness.
JONATHAN: Ichabod’s thoughts exactly. Those were NOT Powder’s hooves thumping.
REDGE: SOMEONE WAS FOLLOWING THEM!
JONATHAN: But as Ichabod nervously urged Powder along, the thumping became muffled. And Ichabod convinced himself there was nothing to be afraid of.
ICHABOD: Must be the wind blowing through the trees..
JONATHAN: He reassured himself, as he pushed on. But soon, he started hearing twigs crack and leaves rustling behind him…
REDGE: My goodness, you were RIGHT, my quills are on end!
JONATHAN: They’re always that way buddy.
REDGE: True, but I’m getting spooked!
JONATHAN: So was Ichabod. He whipped his superstitious head around, fearful of what he might see, and who did Ichabod spy, but THE HEADLESS HORSEMAN from BROM’S STORY! (Headless horseman evil laugh)
REDGE: OH goodness!
JONATHAN: Right! Ichabod feared for his life as he raced through the woods to get home. (horse galloping sound) He was only a field and a bridge away from the safety of the town, but the headless horseman wouldn’t let up! (horse galloping with overlay of Headless Horseman evil laugh) When they entered the field, the horseman drew his sword from its scabbard. (drawing a sword sound)
REDGE: Uh oh.
JONATHAN: And with no other choice, Ichabod drew his sword en garde. (repeat of drawing a sword) He was much smaller than the horseman but all those years of jumping about while teaching, catching books in the shop, and parrying aside so he didn’t walk under a ladder not only made Ichabod a good dancer...but also…
REDGE: ...a great sword fighter?!
JONATHAN: Well I wouldn’t say he was “great,” but Ichabod was quick on his feet, so he could hold his own. And hold his own he did! Circling through the field the two fought, with Ichabod dodging every swing of the horseman’s sword, and even taking a few swings back himself.
REDGE: YAY! Go Ichabod! I’m sorry I said you had a silly name!
JONATHAN: After the back-and-forth play of the blades, Ichabod managed to jump back onto Powder, and head for the town bridge by moonlight. He was inches away from safety.
REDGE: Did he make it?! DID HE MAKE IT?!
JONATHAN: He did.
REDGE: Phew!
JONATHAN: But not before looking back across the bridge to see the headless horseman holding a flaming Jack-O-lantern, with a sinister grin full of fire! He hurled it across the bridge directly at Ichabod!
REDGE: Oh no!
JONATHAN: Oh yes! And the next morning when the town woke at dawn, they discovered that Ichabod Crane never returned home from the party the night before. When his father located his hat and Powder’s hoofprints near the bridge he organized a search party. The only clues they found were pieces of smashed pumpkin.
REDGE: Was the headless horseman Brom Bones or a ghost?!
JONATHAN: We don’t know. All we know is that Ichabod Crane was never seen again. (Headless horseman evil laugh)
REDGE: ...Jonathan. That WAS a very scary tale with an unhappy ending!
JONATHAN: Well, we don’t really know what happened to Ichabod. It’s a mystery not an ending.
REDGE: Though it does have the title of a bedtime story…
JONATHAN: What did we learn about judging a book by its cover...or a person by their name?
REDGE: Right. I’m going to stop doing that at once.
JONATHAN: Plus, we love the oddballs of the world. We ARE the oddballs!
REDGE: You’re so right, Jonathan. Through and through. Well that really was a great way to get in the mood for trick-or-treating…
JONATHAN: But you’re not moving. Don’t you want to meet Thomas the Turtle and the Loppy sisters?
REDGE: Jonathan. Now don’t take this the wrong way, but I think I’m scared stuck. Will you come too for our protection?
JONATHAN: You sure you want me to be your ghost buster, Redge?
REDGE: Yes please!
JONATHAN: Okay, I’ll tag along and watch your back. It’ll be fun. I’ll leave a bowl here for the trick-or-treaters who come to the door.
REDGE: Oh goody! Thank you! Don’t forget your broom, Dumbledore!
JONATHAN: It’s a wizard staff! I’m not Dumbledore, I’m GANDA-! Oh nevermind. Now, be like Sonic the Hedgehog and make speed your second name!
REDGE: Right, we don’t want all the good candy to be gone by the time we get out there!
JONATHAN: (Crypt Keeper Voice and organ music) Or get caught by the headless horseman and his grinning jack o’ lantern. Mwahahahahahaha!
JONATHAN as Crypt Keeper: So remember kiddies, next time you take a short cut, watch out for your heads. (Crypt Keeper laugh)
JONATHAN: This has been a Jonincharacter production. Today’s story was written by Amy Thompson, edited by Molly Murphy and performed by Jonathan Cormur. Sound recording and production by Jermaine Hamilton at Hamilton Studios. Reach out to us on Instagram or email us at dorktalesstorytime@gmail.com. Find links in the show notes or go to dorktalesstorytime.com.
Now, go be the hero of your own story and we’ll see you next once-upon-a-time!
