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😂35 designs · Updated for 2026

Family Funny Pumpkin Cutouts

Looking for family funny pumpkin cutouts? You're in the right place. Print at 100% scale, tape it to your pumpkin, and poke through the lines with a pin.

Browse 35 designs ↓

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Print, tape it to your pumpkin, trace the lines, and start carving.

35 family funny pumpkin cutouts

Beginner or pro, there's something on this page for you.

Intermediate

Five Star Band and Ten Circles

Designed for a long pumpkin lying on its side, this pattern runs a band of five bold stars across the middle with ten round holes scattered above and below like floating orbs. Every star and circle is a simple cut-through, and the sideways layout makes it a fun tabletop centerpiece instead of an upright face. At medium difficulty the stars are the focus: poke each star's five points before cutting so the angles meet sharply.

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Intermediate

Plain Thumbs Up Relief

The classic thumbs-up hand, thumb raised high over four curled fingers, presented as a bold etched panel on the pumpkin's face. No holes are pierced; you shave the outer skin inside the hand outline so the pale flesh forms the gesture, leaving thin rind lines to separate the fingers. Keep the shaved depth even and stop at each finger line so the knuckle ridges stay dark and readable.

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Intermediate

Split Tooth and Two Sparkles

A giant molar with a split between its two roots gleams at the center, flanked by a four-point sparkle on each side and two small dot accents. The tooth outline is cut through around its lobed crown and twin roots, and the sparkles and dots are pierced as well, making a bright emblem any dentist would love. At medium difficulty, the pinch between the roots is the tightest cut, so saw into that notch from both sides and go slow.

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Intermediate

Sleepy Eyes and Eight Lashes

Two closed crescent eyes with four little lashes apiece rest above a small oval mouth, while round dots on each side form rosy cheeks for a sweetly sleeping face. Every crescent, lash, dot, and the mouth is pierced through, so the tiny lash cuts do the expressive work. Cut the two big crescents first, then add the short lash strokes with a fine saw, keeping each one clear of its neighbor.

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Intermediate

Wink and Five Rounded Gaps

One eye is a jaunty upswept crescent wink while the other stays a wide triangle, set over a small diamond nose and a lopsided grin broken into five rounded gaps by chunky teeth. The eyes, nose, and mouth gaps are cut through, leaving the tooth shapes as attached skin between them. A medium carver should cut the five mouth gaps individually rather than one big mouth, which keeps every tooth solidly connected and the crooked smile intact.

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Intermediate

Winking Seven-Tooth Grin

A goofy winking jack-o'-lantern with one wide round eye, one squinting wink, a triangle nose, and an enormous grin broken up by a jumble of square and pointed teeth along both lips. Every feature is cut clean through so the mismatched expression beams from the whole face. At medium difficulty the mouth is the main event; cut the grin outline first, then shape each tooth individually, alternating sides so the lip strips stay supported.

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Intermediate

Cyclops Eye and Five Teeth

A goofy cyclops with one giant round eye under a curly brow, a small triangle nose, freckle dots on each cheek, and a huge laughing mouth with five stubby teeth. The features are cut through, and the pupil stays in place as an attached tab hanging inside the enormous eye. That pupil bridge is the medium-level test; cut both sides of the tab before freeing the rest of the eye circle.

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Intermediate

Wink and Barred Square Grin

One huge round eye stares while the other squeezes into a curled wink above a giant open grin packed with blocky square teeth, and freckle dots sprinkle each cheek. The eyes, mouth, and freckles all cut through the wall, with skin bridges left in place to form the teeth. Cut the mouth's outer outline first, then remove the gaps between teeth one at a time so each block stays anchored.

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Intermediate

Crossed Eyes and Buck Teeth

Huge crossed googly eyes sit under raised brow slots while a gaping oval mouth shows off two goofy buck teeth, with freckle dots on each cheek. The eyes, brows, mouth, and dots are all pierced through, and the dark pupils and teeth are rind left attached inside the openings. Those attached pupils and teeth are the tricky bit; cut around them slowly and leave their connecting bridges generously wide.

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Intermediate

Teardrop Eyes and Three Stars

Two enormous teardrop eyes dominate this quirky alien mug, floating above a tiny triangle nose and a crooked grin made of separate oval mouth slots, with three little stars sprinkled around the face. Every eye, slot, and star is cut through, giving the pumpkin a goofy otherworldly stare. At medium difficulty, carve the huge eyes last since removing that much wall weakens the face, and keep the small oval grin slots evenly spaced.

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Intermediate

Raised Brows and Four Tears

A theatrically miserable pumpkin with worried brows arched high, drooping oval eyes, four teardrops sliding down the cheeks, and a deep downturned frown showing a hint of teeth. Every brow, eye, tear, and the big frown is cut through so the whole sob story glows. A medium carve that lands the joke best when the tears line up; cut the small teardrops first, then the eyes, saving the wide mouth for the end.

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Intermediate

Wide Eyes and Eight Cheek Dots

Raised eyebrow slivers arc over two huge oval eyes, while a big O shaped mouth gasps below and four round dots freckle each cheek. All the openings are simple pierced shapes, but their sheer number bumps this into medium territory. Drill or core the eight cheek dots first while the wall is still strong, then cut the large eyes and mouth so the face keeps its comic shocked stare.

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