Headless Horseman Jokes

Headless Horseman jokes that are clean and safe for kids of all ages. The best Headless Horseman jokes collection for kids, parents, teachers and adults of all ages.

These Headless Horseman jokes are perfect for Halloween but get laughs all year round – especially with the popularity of Ichabod Crane and the Legend of Sleepy Hollow.

According to the legend, the Headless Horseman throws his pumpkin head at Ichabod Crane as he chases him through Sleepy Hollow.

Other names commonly associated with the Headless Horseman legend include Dullahan, Dulachán, Dark Man, Ewen and Headless Jack. Other characters from the Legend of Sleepy Hollow include Ichabod Crane, Katrina Van Tassel and Brom Van Brunt.

Since the Headless Horseman is essentially a ghost, you should also check out our collection of Ghoul jokes and Ghost Jokes. For Halloween Jokes, check out these 150+ Halloween Jokes for Kids or our listing of Halloween Joke Collections (dozens of topics, 1000’s of jokes).

Headless Horseman Jokes for Kids

Q: Why was the Headless Horseman late to the Halloween Party?
A: He overslept – because he was in Sleepy Hollow!

Q: What kind of mood was the Headless Horseman in?
A: He was feeling bloooooo.

Q: What did Katrina think the Headless Horseman was ill?
A: He had a green pumpkin for a head…

Q: What did they call the Headless Horseman after he bragged about scaring Ichabod?
A: A boasty ghosty.

Q: What did the Headless Horseman wear on his feet?
A: Boooots.

More Jokes Continue Below ↓ ↓

Q: How did the Headless Horseman know his future?
A: He read his horror-scope.

Q: Where did the Headless Horseman go surfing?
A: The Dead Sea.

Q: Was the Headless Horseman handsome?
A: Yes, he was gourd-geous.

Q: When did the Headless Horseman’s head stop being a pumpkin?
A: When he threw it – then it was a squash!

Q: What kind of horses did the Headless Horseman ride?
A: Night-MARES. (mares are adult female horses)

Q: Where did Headless Horseman mail letters from?
A: The ghost office.

Q: How did the Headless Horseman stay awake in Sleepy Hollow?
A: Lots of coffee with scream and sugar.

Q: Where did the Headless Horseman shop for clothes?
A: At a boo-tiques.

Q: What did the Headless Horseman give Katrina Van Tassel?
A: A boo-quet of flowers.

Q: How did the the Headless Horseman keep his feet dry?
A: He wore ghoul-oshes.

Q: What was Ichabod Crane afraid of?
A: Things that go Pumpkin the night…

Q: Why wasn’t the Headless Horseman so smart?
A: Because he had all his brains scooped out (pumpkin head).

More Jokes Continue Below ↓ ↓

Q: How did the Headless Horseman fix his head?
A: With a pumpkin patch.

Q: What Viking ghost comes out every Halloween night?
A: The Headless Norseman…

Q: What does the Headless Horseman serve for dessert?
A: Ice Scream.

Q: What was the Headless Horseman’s favorite game?
A: Hide-and-Go-Shriek.

Q: What did the Headless Horseman do after he left Sleepy Hollow?
A: He joined the Ghost Guard.

Q: Why was the Headless Horseman given a ticket by the game warden?
A: He didn’t have a haunting license.

Q: Which lake did the Headless Horseman like to go fishing?
A: Lake Eerie.

Q: How did the Headless Horseman get around when he didn’t have a horse?
A: On his boocycle.

Q: What kind of mistakes did the Headless Horseman make?
A: Boo-boos.

Q: Why did the Headless Horseman like organic pumpkins?
A: Because they are super-natural.

Q: What was the Headless Horseman’s favorite day of the week?
A: Frightday.

Still More Jokes Below ↓ ↓

Q: What type of animal did the Headless Horseman keep as a pet?
A: A scare crow.

Make sure check out our collection of spooky Ghoul jokes and Ghost Jokes. For Halloween Jokes, check out these 150+ Halloween Jokes for Kids or our listing of Halloween Joke Collections (dozens of topics, 1000’s of jokes).

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