We sometimes include affiliate links and curated AI content to highlight top design styles.
Nothing screams Halloween quite like a carved pumpkin—especially when it’s filled with humor, creativity, and spookiness. In this collection, we’ve gathered 21 of the most hilariously awesome pumpkin carvings out there, each one totally real and bursting with personality.
Get ready to laugh, get inspired, and maybe even find your next carving challenge. Let’s dive into the pumpkin patch and see what kind of mischief these hilarious gourds are up to!
1. The Grin Twins: Carved Chaos Meets Cheeky Smiles
These two pumpkins are like the mischievous siblings of Halloween—they’re all about those creepy grins! One sports a toothy smile that’s half “Oops, did I eat all the candy?” and half monster-in-the-closet vibes, with sharp, daring white fangs for extra bite. The other has a more classic gaping look, almost like it’s perpetually gasping in spooky shock. Together, they make the perfect pair to guard your porch—one laughs, the other looms, and both are up to no good!
2. The Pumpkin Burger Binge: Jack’s Midnight Snack
This guy looks like he’s seriously craving some late-night comfort food—nothing like a big ol’ pumpkin burger to hit the spot! With a wickedly happy grin and eyes narrowed in delicious focus, this jack-o’-lantern has gone full foodie. The “burger” even comes with pumpkin seed “sesame” for extra flair!
If you want your Halloween decor to show off some humor and a bit of quirky culinary charm, this munching pumpkin is the perfect centerpiece. Just don’t let it near the candy stash—he might decide it’s dessert time next!
3. The Spooky Cat Silhouette: Feline Frights Ahead
Nothing says Halloween quite like a black cat—especially one that looks this stylishly spooky! This pumpkin features a sleek, arched-back kitty with a tail that spirals into a perfect curl, ready to pounce on any ghostly trouble lurking around. With its elegant yet eerie silhouette, this design adds a touch of classic Halloween charm to your porch.
It’s the perfect choice for all the cat lovers out there who want their jack-o’-lantern to be more chic than chilling. Just be sure to keep an eye out—this feline might have nine ghostly lives!
4. The Happy Halloween Grinner: Say It with a Smile!
This pumpkin is all about spreading Halloween cheer—literally! With the words “HAPPY HALLOWEEN” carved into its massive grin, it’s both a greeting and a decoration rolled into one. The big googly eyes and raised eyebrows give it an enthusiastic, slightly manic vibe—like it’s the friend who shows up to the party in full costume while everyone else is still figuring out what to wear.
This bold design is perfect for welcoming trick-or-treaters and letting everyone know you’re all-in for the spooky festivities—no ghost left behind!
5. The Pumpkin Totem: Triple Trouble Stack
Why settle for just one pumpkin when you can have a whole goofy gang? This stacked pumpkin totem has three hilarious personalities—each more quirky than the last. From the wild-eyed top pumpkin sporting an eager grin to the tongue-wagging goof in the middle, and the skeptical smirk of the bottom one, this trio has the whole range of Halloween emotions covered!
With a friendly skeleton photobombing in the background, it’s like they’re a comedy team ready to put on a spooky show. Perfect for those who want to take their Halloween decorating game to new heights—literally!
6. The Pumpkin Demon: Lurking in the Shadows
This pumpkin is taking “scary” to a whole new level—meet the demon who’s ready to haunt your Halloween! With jagged horns, piercing eyes, and monstrous claws, it looks like it’s about to leap out from the pumpkin and into the night. This design is perfect if you’re going for a sinister vibe that will make trick-or-treaters think twice before approaching your porch.
It’s spooky, detailed, and oh-so-dramatic—ideal for anyone who wants their pumpkin carving to channel a bit of that old-school Halloween horror. Just remember, it’s all good fun, right?
7. The Arachnophobia Pumpkin: Creepy Crawly Surprise
Uh-oh, this pumpkin seems to have unexpected guests! With a wide-eyed expression of pure, cartoonish terror, it’s clear that this jack-o’-lantern is not thrilled about the plastic spiders scaling its face. Perfect for adding a dose of humor to your Halloween decorations, this scaredy-pumpkin captures exactly how a lot of us feel about creepy crawlies.
Those simple, exaggerated eyes and quivering lip make it adorably relatable, while the fake spiders crawling across add that extra dose of spookiness. It’s the ultimate combination of cute and creepy—perfect for arachnophobes with a sense of humor!
8. The Spirited Swirl Pumpkin: Ghostly Giggles
This whimsical pumpkin design brings out the playful spirit of Halloween! With swirling eyes that spiral inward and a wavy mouth that looks like it’s caught mid-giggle, this jack-o’-lantern is more cute than creepy. It’s like the pumpkin itself is laughing at its own ghostly joke, adding a dash of lighthearted fun to your decorations.
Perfect for those who prefer charm over chills, this swirly-eyed character will put a smile on everyone’s face—after all, Halloween should be as much about the laughs as it is the scares!
9. The Winking Jack: Flirty and Fun
Who knew pumpkins could be such charmers? This jack-o’-lantern is all about personality, sporting a big, confident wink and a smile that says, “Who’s ready for some spooky fun?” This lighthearted design is perfect if you want to bring some cheekiness to your Halloween display—it’s friendly, flirty, and totally unbothered by all the ghostly antics around it.
Whether you’re trying to make trick-or-treaters giggle or just looking for something that stands out from the usual scare-fest, this winking pumpkin will add that irresistible, fun vibe to your Halloween setup.
10. The Friendly Ghost Pumpkin: Boo-tifully Charming
Say hello to this jolly little ghost—he’s less about scaring and more about spreading Halloween cheer! With outstretched arms and a happy expression, this ghostly jack-o’-lantern is the perfect way to add some light-hearted, spooky spirit to your decor. Whether it’s greeting trick-or-treaters or keeping the front porch company, this ghost is all about the “boo” without the “hoo.”
It’s great for those who want a classic Halloween figure that’s more adorable than alarming—because sometimes, even the afterlife needs a bit of charm and good vibes!
11. The Pumpkin Cannibal: The Snack Attack Strikes!
This jack-o’-lantern isn’t just here for decoration—it came for a meal! With its fierce eyes and wickedly jagged grin, this pumpkin’s up to no good, chomping down on a smaller, terrified mini-pumpkin caught between its menacing teeth. The expression of pure mischief on this larger pumpkin says it all—it’s all about trick and treat!
Perfect for those who want their Halloween display to be just a bit wicked, this cannibalistic creation brings the ultimate creepy factor to your porch. Beware, no small pumpkins are safe when this hungry beast is on the scene!
12. The Spiked Trap Pumpkin: A Prickly Predicament
This poor little mini-pumpkin has found itself in quite the sticky situation—literally! The large pumpkin’s gaping mouth is lined with sharp, toothpick-like spikes, creating a dramatic scene of impending doom for its unlucky snack. The wide-eyed, terrified expression on the smaller pumpkin makes it look like it just realized it’s in big trouble.
This design is a fantastic twist for those who want their Halloween decor to be a bit edgier—pun intended! It’s equal parts comical and creepy, making it a standout piece that adds a touch of wicked humor to any festive setup.
13. The Moo-tastic Pumpkin: Cow-lantern Cutie
Who said jack-o’-lanterns have to be scary? This pumpkin has traded in spooky for utterly adorable! With cow-like spots, cute little carved ears, and a snout-like mouth, this cow-themed jack-o’-lantern is bringing all the farm vibes to Halloween. This delightful “moo-lantern” will surely be the most charming gourd on the block, perfect for those who want to add a touch of whimsy rather than fright. It’s a great choice if you want to carve up something different this year that’ll leave everyone saying, “Holy cow, that’s cute!”
14. The Ghostbuster Pumpkin: Who Ya Gonna Call?
This pumpkin is all about the nostalgia—featuring the iconic “No Ghosts” symbol that every Ghostbusters fan knows and loves! With a friendly yet slightly frightened little ghost encased in the classic barred circle, this carving takes a playful jab at the spirit world, just like our favorite ghost-hunting heroes.
Whether you’re a fan of the classic ’80s flick or just love the idea of keeping your porch ghost-free, this design is sure to get some smiles—and maybe a few humming that unforgettable theme song. Because let’s face it, when it comes to spooks, who ya gonna call?
15. The Startled Pumpkin
This pumpkin looks like it’s just seen a ghost—and it’s not taking it well! With eyes wide open, eyebrows arched, and a mouth frozen in a startled “Oh no!” expression, this jack-o’-lantern perfectly captures that moment of unexpected terror. The exaggerated features and comically large eyes give it a playful twist, making it more funny than frightening.
This is the perfect design for anyone who wants to add a bit of Halloween humor to their porch—it’s a jack-o’-lantern that knows exactly how you feel when something goes “bump” in the night!
16. The Skeletal Smirk Pumpkin: Mischievously Spooky
This pumpkin has taken a page out of the classic skeleton look, complete with stitched-up lips and an expression full of mischievous glee. One eye is arched in a playful brow-raise, and the mouth is a neat set of carved lines that give off serious “Nightmare Before Christmas” vibes. It’s not quite a smile, more of a “What are you up to this Halloween?” sort of look.
Perfect for anyone who loves a dash of spooky attitude, this carved creation will bring some bone-chilling charm to your doorstep—just the right amount of playful spookiness for any Halloween fan!
17. The Hangry Pumpkin: Gourd-eating Gourd
This pumpkin isn’t just hungry—it’s hangry, and it’s taking its frustration out on a poor little mini-pumpkin! With bulging eyes and a fierce scowl, this big jack-o’-lantern is going full monster mode, chomping down on a smaller pumpkin that looks absolutely terrified. The mini pumpkin’s stem even sticks out like a desperate plea for help—too late, little buddy!
This hilarious yet dramatic design is perfect for those who love adding a sense of chaotic humor to their Halloween decorations. It’s a wild blend of funny, creepy, and creatively over-the-top—ideal for giving your display a real bite!
18. The Winking Smiley Pumpkin: Mischief and Mayhem
This pumpkin is all charm and cheekiness, with a winking star-shaped eye and a massive grin full of delightfully gnarly teeth! It looks like it’s just pulled off a successful prank or heard the best Halloween joke ever. The winking expression gives it a playfully conspiratorial vibe—like it’s letting you in on a secret, and its gigantic smile is all about having the best spooky season ever.
Perfect for those who prefer their jack-o’-lanterns full of personality and humor, this pumpkin will add a bright, mischievous touch to any Halloween setup!
19. The Batty Pumpkin: Winged and Wicked
This pumpkin is bringing the Halloween vibes straight out of a spooky cartoon! Carved with an adorably ominous bat figure, complete with outstretched wings and a broad grin, it’s the perfect mix of eerie and endearing. The glowing light from within makes the bat look like it’s in mid-flight, ready to soar into the night sky.
This design is ideal for anyone who wants to add some classic Halloween flair without the heavy frights—a light-hearted homage to the batty creatures of the night that will surely charm both kids and adults alike!
20. The Grinning Gargantua: A Toothsome Terror
This massive jack-o’-lantern brings the nightmare fuel with its ridiculously huge grin and rows of sharp, exaggerated teeth. Its menacing, half-lidded eyes add to the sinister vibe, like it knows something you don’t—and it’s relishing the thought! This is the kind of pumpkin that looks like it might come alive at midnight, ready to chomp down on whatever’s in its way.
Perfect for adding a seriously scary centerpiece to your Halloween display, this design will guarantee wide-eyed wonder—and maybe a few shivers—from everyone who dares to approach. It’s a true testament to the art of pumpkin-carving horror!
21. The “I Ate Too Much” Pumpkin: A Gory Farewell
Our final pumpkin is the ultimate embodiment of Halloween excess—a big jack-o’-lantern gobbling up a smaller pumpkin, and regretting every bite! With seeds and pulp spilling out like a ghastly mess, the smaller pumpkin seems to have made one heck of an escape attempt, leaving a trail of stringy pumpkin guts behind.
It’s a hilariously graphic and gross way to say goodbye to our pumpkin gallery! If you’ve enjoyed these wild and wacky pumpkin designs, take some inspiration, grab your carving tools, and get creative this Halloween. Remember—sometimes it’s all about carving out a little chaos!
