25 Intermediate Silly Pumpkin Stencils

25 printable intermediate silly pumpkin stencils — ready to download, trace, and light up the porch.

1. 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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2. 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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3. 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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4. 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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5. 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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6. 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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7. 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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8. 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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9. 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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10. Unequal Eyes and Crooked Teeth
This lovably lopsided face pairs one round eye with one droopy crescent eye, a triangle nose, and a huge crooked grin full of uneven square teeth, plus a pair of dot dimples on each cheek. The eyes, nose, mouth, and dots are pierced while the mismatched tooth bars stay attached. It suits odd-shaped pumpkins perfectly; cut the tooth gaps in random sizes and the wonkier it looks, the better.
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11. Barred Eyes and Cheek Tears
A goofy clown face with big round eyes crossed by horizontal rind bars, teardrop shapes dangling from each cheek, a button nose, and a huge grin with three chunky teeth. The eyes, tears, nose, and mouth are all cut through, while the eye bars and teeth stay as attached rind bridges. Those bars make it a medium carve: cut each eye as an upper and lower opening on either side of the bar, supporting the bridge with a finger as you finish the strokes.
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12. Three Eyes and Rounded Teeth
Three round eyes line up across the brow of this cheerful monster, above a wide grinning mouth with four rounded teeth hanging from the top lip and a small diamond accent cut on each cheek. The eyes, diamonds, and mouth are cut through, with the teeth left attached to the upper mouth edge. At medium difficulty, the main care point is those hanging teeth: cut around each one gently, and try it on a green or warty pumpkin for extra monster energy.
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13. Three Eyes and Four Teeth
Three round eyes of different sizes line up above a small rectangular nose and a wavy grin broken by four square teeth, giving this mutant jack-o'-lantern a delightfully goofy personality. The eyes, nose, and mouth are all cut through, with the teeth left as tabs, and tiny freckle dots may be etched shallow on the cheeks. A medium carve mainly for tooth care; cut into the grin from between the teeth so each square tab keeps its corners.
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14. Right Wink and Eight Freckles
A winking smiley with one open eye, one curved wink swoosh, a big grin holding a single square tooth, and a cluster of four freckle dots on each cheek. All shapes cut through, and the tiny freckles are what nudge this to medium difficulty. Punch the dots with a drill bit or apple corer before sawing the larger openings, since small circles are far easier while the wall is intact.
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15. Left Wink and Six Cheek Wedges
A playful winking jack-o'-lantern: one big round open eye, one arched wink, a triangle nose, and a smiling mouth with blocky teeth, all framed by three thin whisker-like wedges slashed across each cheek. Every opening is cut through, and the six cheek wedges throw extra slivers of light. At medium difficulty, cut the large features first and finish with the skinny cheek slits, using a fine saw so each wedge tapers to a clean point.
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16. Tall Smile and Six Cheek Dots
A tall pumpkin design with arched happy eyes, an oval nose, three dot freckles on each cheek, and a huge open smile with four little teeth hanging from the top lip. Every shape is cut through, and the six small cheek dots add a sprinkle of glowing freckles around the grin. Punch the freckle dots with an apple corer or drill bit before opening the big mouth.
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17. Round-Eyed Clown With Brows
A cheerful clown face with raised curving brows, big round eyes, a round button nose, small dot cheeks, and a huge sweeping smile. Every feature is a straightforward cut-through opening, and the little cheek dots on each side add extra sparkle at night. At medium difficulty the challenge is spacing: transfer the stencil carefully so the brows sit clear of the eyes, then drill the small dots with a pumpkin drill or apple corer for perfect circles.
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18. Fishbone Skeleton
A cartoon fish skeleton stretches across the pumpkin, complete with an open-mouthed head, a round eye, a long spine lined with curved rib bones, and a fanned tail. The whole design is skin-shaved rather than pierced, so the pale bones glow softly against the dark rind like an x-ray. For this medium etch, outline the spine first, then shave each rib in one smooth stroke so the curves stay parallel and evenly spaced.
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19. Ostrich & Feathered Rump
A full-body ostrich stands in profile, with its long curved neck, round feathered body, and two lanky legs shaved into the pumpkin skin. Nothing is pierced; you peel away the skin inside the bird so the pale flesh forms a two-tone silhouette against the orange shell. Use a loop tool or vegetable peeler and shave in shallow passes so the thin neck and legs stay even in width.
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20. One-Eye Arched-Brow Smile
A single giant eye dominates this friendly monster face, with a dark round pupil left in place at its center and a curved brow arched above. Below, a huge grin sweeps ear to ear with pointed dimples at each corner. The eye ring, brow, and smile are cut through while the pupil stays as an island of shell, which is what earns the medium rating; anchor that pupil with a toothpick from behind if it feels loose.
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21. One Eye and Two Upper Teeth
A goofy one-eyed jack-o'-lantern with a huge round eye topped by a dark pupil circle, a small triangle nose, and a wide smile broken by two chunky upper teeth. The big eye, nose, and mouth are cut through, while the pupil area keeps a disc of skin attached at the top for contrast. Support the teeth by cutting away from their narrow roots, since those two tabs carry the whole grin.
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22. Wink and Split-Tongue Smile
A playful winking face sticks its tongue out at trick-or-treaters: one round eye is a full cutout, the other a squeezed-shut winking arc, above a wide grin with a dangling split tongue. The face ring, eyes, and mouth are pierced through while the tongue stays attached as a bridge of pumpkin. Cut around the tongue last and leave it slightly thicker than the line for strength.
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23. Anxious Round-Pupil Frown
A hilariously worried pumpkin face with two big round eyes topped by drooping eyebrow arcs and a deep upside-down frown. Each feature is a pierced opening, and the round pupils stay attached as tabs inside the glowing eyes to give it that anxious stare. At medium difficulty the pupil bridges are the key detail; cut toward each tab rather than away so you do not snap them off.
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24. Uneven Eyes and Five Teeth
A mischievous jack-o'-lantern with deliberately uneven eyes under slanted brows, a triangle nose, and a huge crooked grin interrupted by five hanging teeth. All the features are pierced clean through so candlelight pours out of every gap. The teeth are the trickiest part at this medium level, so cut around each one slowly and leave those tabs attached to the rim of the mouth.
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25. Lopsided Zigzag Grin
A cheerfully lopsided jack-o'-lantern face with one big round eye, one slanted triangle eye, and a wide zigzag grin stretching across the pumpkin. All three features are pierced fully through so candlelight pours out, while the surrounding skin stays untouched. The zigzag mouth is the trickiest part at this medium level, so cut each tooth point in two short strokes that meet at the tip instead of dragging one long sawing pass.
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