Halloween is all about spooky fun, costumes, and sweet treats. And what better way to celebrate than with some brain-teasing riddles inspired by Charlie Brown and the Peanuts gang? These riddles will have you laughing, thinking, and maybe even scratching your head. Charlie Brown Halloween Riddles.
Whether you’re hosting a Halloween party, trick-or-treating, or just want some festive fun, these riddles are perfect for all ages. Get ready to dive into the Great Pumpkin’s world of mystery, humor, and surprises!
The Great Pumpkin’s Trick-or-Treat Riddles
- Why did the Great Pumpkin refuse to rise from the patch?
Because he was feeling a little vine-tangled! - What’s the Great Pumpkin’s favorite sport?
Squash! - Why did Linus bring a ladder to the pumpkin patch?
To reach new heights of belief! - How does the Great Pumpkin celebrate Halloween?
By making gourd-geous appearances! - What’s the Great Pumpkin’s favorite type of music?
Pumpkin’ rock! - Why don’t pumpkins argue?
Because they squash their problems! - What’s Linus’s favorite Halloween snack?
Pumpkin pie with a side of hope! - Why did Charlie Brown look confused at the pumpkin patch?
Because he was searching for the “Great” in it! - What did the Great Pumpkin say to the little pumpkins?
“Orange you excited for Halloween?” - How do pumpkins get into shape for Halloween?
They do plenty of jack-o’-cises! - Why did the pumpkin sit in the corner?
Because it was a little “patchy” on directions! - What’s the Great Pumpkin’s favorite holiday besides Halloween?
Thanksgiving—because of all the pie! - Why did the scarecrow refuse to believe in the Great Pumpkin?
He had too much straw in his head to think about it! - Why do ghosts love the Great Pumpkin?
Because he’s always a “boo-tiful” sight! - What’s the Great Pumpkin’s favorite dance move?
The Vine Twist! - Why did Lucy roll her eyes at Linus on Halloween?
Because she knew she wouldn’t get any candy in the pumpkin patch! - What did the Great Pumpkin say before leaving?
“I’ll be gourd to see you next year!” - Why do pumpkins tell the best jokes?
Because they have gourd timing! - What happens when the Great Pumpkin tells a scary story?
Everyone gets “squashed” with fear!
Read More: Bonfire Riddles
Spooky Peanuts Halloween Riddles
- Why didn’t Charlie Brown ever get a good Halloween treat?
Because he always got a rock! - What did Sally say when Linus invited her to wait for the Great Pumpkin?
“I’ll only come if there’s candy involved!” - Why did Snoopy wear a ghost costume?
To prove that beagles can be spooky too! - How does Woodstock celebrate Halloween?
With a “tweet” or treat! - Why did Lucy refuse to wait for the Great Pumpkin?
She knew it was just a “patch” of trouble! - What’s the scariest thing in Charlie Brown’s life?
Lucy’s football tricks! - Why did Schroeder bring a piano to the pumpkin patch?
To play haunting melodies for the Great Pumpkin! - What do the Peanuts characters say after trick-or-treating?
“We got candy, but Charlie Brown got a rock!” - Why did Snoopy dress as a vampire?
Because he wanted to be Count Beagula! - What’s Linus’s biggest Halloween fear?
Missing the Great Pumpkin’s arrival! - Why did Peppermint Patty think Halloween was unfair?
Because Marcie got better candy than her! - What’s the best Halloween joke in Peanuts?
Lucy convincing Charlie Brown she won’t pull the football away! - Why did Sally call Halloween the worst holiday?
Because waiting in a pumpkin patch wasn’t her idea of fun! - How do Peanuts characters solve their Halloween problems?
They just “Peanut” through! - Why did Franklin wear sunglasses on Halloween night?
To be the coolest trick-or-treater in town! - What’s Snoopy’s favorite Halloween snack?
Dog bone candy! - Why did Linus bring a camera to the pumpkin patch?
To snap a photo of the Great Pumpkin! - What’s Charlie Brown’s favorite Halloween phrase?
“I got a rock…” - Why did Marcie stay home on Halloween?
Because she thought trick-or-treating was too much work!
Ghostly Giggles with Snoopy
- Why did Snoopy dress as a skeleton for Halloween?
Because he wanted to “bone” up on his costume skills! - What did Woodstock say when he saw a ghost?
“Tweet or treat!” - Why did Snoopy bring a flashlight to the pumpkin patch?
To make sure the Great Pumpkin could see him! - What’s Snoopy’s favorite Halloween game?
Hide and “squeak!” - Why don’t ghosts haunt Snoopy?
Because he’s too “paws-itively” fearless! - What do you call Snoopy’s haunted doghouse?
The Boo-dog Mansion! - Why did Linus ask Snoopy to wait for the Great Pumpkin?
Because even a beagle has better luck than him! - What’s Snoopy’s Halloween catchphrase?
“Boo-bidly-bark!” - Why did Snoopy carve a bone-shaped pumpkin?
Because it was “howl-o-ween!” - What did Woodstock and Snoopy wear as a duo costume?
A ghost and a vampire bat! - Why did Snoopy howl at the moon on Halloween?
Because it was “fur-righteningly” fun! - Why did Charlie Brown give Snoopy extra candy?
Because he deserved better than a rock! - What’s Snoopy’s scariest Halloween nightmare?
Running out of dog treats! - Why did Snoopy bob for apples with his nose?
Because paws don’t work as well! - Why did Snoopy dress as a witch?
To cast a “fetching” spell! - What’s Woodstock’s favorite Halloween tradition?
Flying past the moon like a tiny broomstick! - Why did Snoopy laugh at Linus?
Because he knew the Great Pumpkin was just a myth! - What’s the best Halloween costume for a beagle?
A “barkula” cape! - What did Snoopy do when he got a rock?
Buried it in the backyard!
Lucy’s Halloween Sass
- Why didn’t Lucy believe in the Great Pumpkin?
Because she was too smart for fairy tales! - What’s Lucy’s favorite Halloween trick?
Pulling the football away at the last second! - Why did Lucy wear a crown for Halloween?
Because she always acts like the queen of everything! - What did Lucy say when Charlie Brown got a rock?
“Better luck next year, blockhead!” - Why did Lucy dress as a witch?
Because she already had the attitude for it! - What’s Lucy’s least favorite thing about Halloween?
Sharing her candy! - Why did Lucy roll her eyes at Linus?
Because she knew he’d wait all night for nothing! - What’s Lucy’s idea of a Halloween trick?
Convincing everyone the Great Pumpkin isn’t real! - Why did Lucy refuse to wear a ghost costume?
Because she needed something more fabulous! - What did Lucy call Linus’s Halloween tradition?
A total waste of time! - Why did Lucy eat all her candy at once?
So she wouldn’t have to share with anyone! - What’s Lucy’s biggest Halloween fear?
Someone getting more attention than her! - Why did Lucy dress up as a vampire?
Because she loves to “suck” the fun out of everything! - What’s Lucy’s idea of a good Halloween joke?
Tricking Charlie Brown into thinking he got good candy! - Why did Lucy make fun of Schroeder’s costume?
Because it wasn’t “piano-tastic” enough! - What did Lucy say when Linus asked her to wait for the Great Pumpkin?
“No way! I have better things to do!” - Why did Lucy’s pumpkin carving look perfect?
Because she made sure it was “Lucy-approved!” - What’s Lucy’s favorite thing about Halloween?
Telling everyone else they’re wrong about it! - Why did Lucy dress as a superhero?
Because she already thinks she’s in charge of everything!
Trick-or-Treat Troubles
- Why did Charlie Brown keep getting a rock?
Because his costume was too basic! - Why did Peppermint Patty refuse to wear a ghost costume?
Because she wanted to be something cool, like a pirate! - What did Marcie say when Peppermint Patty asked for help with her costume?
“I think you should just go as yourself!” - Why did Sally demand extra candy?
Because she wasted her time waiting in the pumpkin patch! - Why did Charlie Brown’s ghost costume have too many holes?
Because he messed up cutting it! - What’s the scariest thing about trick-or-treating in Peanuts?
The risk of getting a rock! - Why did Schroeder carry his piano while trick-or-treating?
Because he wanted to play for extra candy! - Why did Linus bring a sleeping bag to the pumpkin patch?
Because he planned to stay all night! - Why did Snoopy get the best candy?
Because he looked too cute to say no to! - Why did Marcie call Halloween confusing?
Because she didn’t understand why people dressed as monsters! - What happened when Sally realized she missed out on trick-or-treating?
She got really mad at Linus! - Why did Peppermint Patty laugh at Charlie Brown’s costume?
Because it looked like Swiss cheese! - What’s the best Halloween strategy in Peanuts?
Avoid trick-or-treating with Charlie Brown! - Why did Woodstock get more candy than Linus?
Because he actually knocked on doors! - Why did Lucy dress as a queen?
Because she always wants to be in charge! - What did Charlie Brown say when he got another rock?
“Maybe next year will be different…” - Why did Linus bring a pumpkin to trick-or-treating?
Because he thought it would attract the Great Pumpkin! - Why did Snoopy win the costume contest?
Because he had the best imagination! - What’s the worst Halloween fate in Peanuts?
Getting stuck in the pumpkin patch all night!
Haunted Halloween Ha-Ha’s
- Why did the Peanuts gang visit a haunted house?
To prove they weren’t scared—except they totally were! - Why did ghosts love hanging out with Charlie Brown?
Because he always felt invisible anyway! - Why did Linus think the haunted house was fake?
Because he was too focused on the Great Pumpkin! - What happened when Snoopy went inside the haunted house?
He turned it into a comedy show! - Why did Lucy bring a mirror to the haunted house?
So she could admire herself even in the dark! - What’s the Peanuts gang’s worst Halloween fear?
Running out of candy! - Why did the haunted house love the Peanuts gang?
Because they were easily spooked! - Why did Woodstock hide behind Snoopy in the haunted house?
Because he didn’t want to be ghost food! - What’s the Great Pumpkin’s favorite haunted house?
One with lots of pumpkins, of course! - Why did Charlie Brown think the haunted house was unfair?
Because even ghosts got better candy than him! - Why did Linus bring a flashlight?
To make sure the Great Pumpkin wasn’t hiding in a dark corner! - What’s the best part of a haunted house?
The candy at the end! - Why did Sally scream in the haunted house?
Because a fake ghost popped out too fast! - What’s Snoopy’s secret weapon against ghosts?
His adorable charm! - Why did Lucy think haunted houses were silly?
Because nothing is scarier than her attitude! - Why did Peppermint Patty think the haunted house was funny?
Because ghosts don’t scare tough kids like her! - What’s the best way to survive a haunted house?
Stick close to Snoopy! - Why did the haunted house love Charlie Brown?
Because he was the easiest to scare! - What’s Linus’s Halloween wish?
To see the Great Pumpkin appear—just once!
The Great Pumpkin’s Silly Secrets
- Why did the Great Pumpkin skip Charlie Brown’s house?
Because he didn’t want to give out rocks too! - Why did Linus refuse to leave the pumpkin patch?
Because he was on a “gourd” mission! - What’s the Great Pumpkin’s favorite kind of music?
Pumpkin rock! - Why did Sally regret waiting for the Great Pumpkin?
Because she missed out on candy! - What’s the Great Pumpkin’s favorite holiday treat?
Pumpkin pie—wait, maybe not! - Why did the Great Pumpkin laugh at Linus?
Because he falls for the same trick every year! - What did Lucy say about the Great Pumpkin?
“That’s the biggest joke I’ve ever heard!” - Why did Linus bring a sign to the pumpkin patch?
To make sure the Great Pumpkin didn’t miss him! - What’s the Great Pumpkin’s favorite game?
Hide and gourd seek! - Why does no one ever see the Great Pumpkin?
Because he’s great at staying hidden! - Why did Charlie Brown try waiting for the Great Pumpkin?
Because he thought he might have better luck than Linus! - What’s the Great Pumpkin’s least favorite thing?
Pumpkin spice everything! - Why did Linus write a letter to the Great Pumpkin?
Because he wanted to make sure he showed up! - What’s the Great Pumpkin’s favorite Halloween tradition?
Surprising Linus with… nothing! - Why did Snoopy dress up as the Great Pumpkin?
To play the ultimate Halloween prank! - What’s the Great Pumpkin’s favorite Halloween snack?
Candy corn, of course! - Why did Lucy roll her eyes at Linus?
Because she knew the Great Pumpkin was just a story! - What’s the Great Pumpkin’s biggest fear?
Being turned into a jack-o’-lantern! - Why does Linus believe in the Great Pumpkin?
Because Halloween magic is real—right?
Linus’s Pumpkin Patch Puzzles
- Why did Linus bring a blanket to the pumpkin patch?
For maximum Halloween coziness! - What’s Linus’s Halloween tradition?
Waiting…and waiting… and waiting… - Why did Linus think the pumpkin patch was the best place?
Because it had the most sincere pumpkins! - Why did Linus get so excited on Halloween night?
Because he thought this was finally the year! - What did Lucy call Linus’s Great Pumpkin plan?
A big waste of time! - Why did Linus pack snacks for the pumpkin patch?
Because waiting all night is hard work! - What did Linus dream about on Halloween?
Finally meeting the Great Pumpkin! - Why did Linus refuse to go trick-or-treating?
Because he had “more important” things to do! - Why did Sally almost leave the pumpkin patch?
Because she realized there was no candy there! - Why did Linus write another letter to the Great Pumpkin?
Because he didn’t want to be forgotten! - What’s Linus’s favorite Halloween word?
Sincerity! - Why did Linus wear a scarf in the pumpkin patch?
Because Halloween nights get chilly! - Why does Linus love pumpkins?
Because they remind him of Halloween magic! - Why did Linus bring a flashlight?
To make sure he didn’t miss anything spooky! - What’s the biggest mystery of Linus’s life?
Why the Great Pumpkin never shows up! - Why did Lucy drag Linus home?
Because he fell asleep in the pumpkin patch! - Why did Linus sigh at the end of Halloween night?
Because the Great Pumpkin was a no-show—again! - What’s Linus’s Halloween wish?
To be proven right—just once! - Why did Linus keep trying every year?
Because he believed in Halloween magic!
Spooky Peanuts Mischief
- Why did Peppermint Patty prank Charlie Brown?
Because Halloween is all about tricks AND treats! - Why did Woodstock hide in Snoopy’s trick-or-treat bag?
Because he wanted to sneak extra candy! - What’s Lucy’s idea of a Halloween joke?
Telling Linus the Great Pumpkin showed up—when he didn’t! - Why did Snoopy pretend to be a ghost?
Because he wanted to spook the Peanuts gang! - Why did Charlie Brown laugh at his own costume?
Because he knew it was a disaster! - Why did Marcie give Peppermint Patty all her candy?
Because she didn’t care much for sweets! - What’s Sally’s biggest Halloween regret?
Believing in Linus’s pumpkin stories! - Why did Schroeder refuse to dress up as a monster?
Because he only wanted to be a musician! - Why did Peppermint Patty dress as a pirate?
Because she’s always ready for adventure! - Why did Lucy keep checking her mirror on Halloween night?
Because she needed to make sure she looked perfect! - What’s the best Halloween prank in Peanuts history?
Lucy making Linus believe the Great Pumpkin was real! - Why did Woodstock try on different costumes?
Because he couldn’t decide which one was cutest! - Why did Linus bring extra blankets?
Because pumpkin patches get cold at night! - What’s Snoopy’s idea of a perfect Halloween?
Eating all the candy before anyone notices! - Why did Charlie Brown sigh at the end of the night?
Because he was stuck with a bunch of rocks! - What’s Lucy’s idea of a “perfect” Halloween?
Getting all the best candy and being the boss! - Why did Schroeder bring his piano trick-or-treating?
Because he thought music would get him more candy! - Why did Snoopy sneak into Linus’s pumpkin patch?
Because he wanted to see what all the fuss was about! - What’s the Peanuts gang’s biggest Halloween mystery?
Why Charlie Brown always gets rocks!
Halloween Night Shenanigans
- Why did Lucy laugh at Linus’s pumpkin speech?
Because she thought it was the silliest thing ever! - Why did Charlie Brown wear his ghost costume wrong?
Because he cut too many eye holes! - Why did Snoopy bring a pillowcase instead of a candy bag?
Because he was planning for a big haul! - Why did Linus stay up way past midnight?
Because he thought the Great Pumpkin might be late! - Why did Lucy storm out of the pumpkin patch?
Because she realized she was wasting her night! - What’s the worst thing about Halloween in Peanuts?
Charlie Brown’s never-ending bad luck! - Why did Peppermint Patty challenge Lucy to a candy contest?
Because she thought she could collect more treats! - What’s Snoopy’s favorite Halloween dance?
The Monster Mash, of course! - Why did Woodstock carry a tiny pumpkin?
Because he wanted to join in on the fun! - Why did Linus refuse to eat pumpkin pie?
Because it felt like a betrayal! - Why did Schroeder bring music to the Halloween party?
Because every celebration needs a soundtrack! - Why did Sally get mad at Linus?
Because she realized she wasted her whole night! - What’s Charlie Brown’s least favorite Halloween tradition?
Getting a bag full of rocks! - Why did Lucy dress as a princess?
Because she always thinks she’s royalty! - Why did the Peanuts gang tell scary stories?
To make Halloween even spookier! - Why did Peppermint Patty wear sunglasses at night?
Because she thought they made her look cooler! - Why did Linus write another letter to the Great Pumpkin?
Because hope never dies! - Why did Woodstock and Snoopy share candy?
Because best friends always share! - What’s the funniest thing about Peanuts Halloween?
Charlie Brown’s bad luck never changes!
Final Thoughts
Charlie Brown and the Peanuts gang make every Halloween special, and these riddles add even more fun to the mix! Whether you’re sharing them with friends, family, or using them for a Halloween party, they bring laughter and excitement to the spooky season.
