25 DIY Smiling Pumpkin Cutouts

Explore 25 distinct diy smiling pumpkin cutouts from the stencil library.

1. Twenty-Two Ray Smiling Sun
A beaming sunburst face with closed happy crescent eyes, a small triangle nose, and a huge picket-tooth grin, all encircled by a radiating ring of alternating teardrop and triangle ray cutouts. Every ray, tooth gap, and feature pierces through, and the sheer count of small openings makes it an expert carve. Cut the outer rays in sequence around the circle first, rotating the pumpkin as you go, before opening the large mouth.
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2. Smiling Arches and Leaf Ring
A mischievous crescent-eyed grin packed with individual teeth sits inside a full ring of diamond and leaf-shaped cutouts, with dozens of small dots sparkling between them. Every element is pierced through, and the sheer number of tiny openings is what earns the expert rating. Drill all the dots first, then saw the border shapes, saving the big fragile mouth for the very end.
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3. Heart Keyholes and Leaf Cheeks
A folk-art beauty: two heart-shaped keyhole eyes crowned with leafy sprigs, sprays of leaf cutouts fanning across both cheeks, diamond accents down the brow, and a huge grin filled with neat rectangular teeth. Every heart, leaf, diamond, and tooth gap is pierced through, creating a lacework of light. This is an expert pattern with many close-set openings, so work from the center outward and rotate the pumpkin often to keep your cutting angle comfortable.
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4. Star Crown and Four Tooth Grin
A crown of small four-point stars sparkles around the top of this face, while two big playful eyes with attached pupil tabs sit over a wide grin lined with little teeth. Everything is cut through, and the pupils survive as tabs rooted to the top of each eye opening. Carve the star crown first while the wall is strongest, then cut each eye around its pupil tab in small strokes so the tabs stay put.
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5. Heart Eyes and Seventeen Gems
The heart-eyes emoji comes to life with two big heart-shaped eyes, arched brows, and a wide toothy smile, all surrounded by seventeen small hearts and diamond accents scattered across the shell. Every heart, brow, tooth gap, and diamond is pierced through, so the whole pumpkin twinkles. Carve the large central face first while the shell is strongest, then work outward through the border hearts from biggest to smallest.
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6. Goofy Pupils and Twelve Dots
A freckle-faced goofball with lifted eyebrow cuts, big eyes crossed by full-width pupil tabs, a round nose, twelve freckle dots, and a huge open grin with mismatched teeth. The openings are cut through while the pupil bars, teeth, and surrounding freckle rind stay intact. It rates hard because those wide pupil tabs span the entire eye: cut each eye as separate top and bottom windows, drill the freckles with a small round bit, and save the eyebrows for last.
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7. Arched Pupils and Twelve Rays
This pumpkin is absolutely thrilled to see you: arched eyes with hanging pupil tabs sit above a giant grin packed with separated square teeth, while short rays burst from each cheek like cartoon sparkle lines. All the shapes cut through, and the many thin bridges between teeth and rays are why it rates hard. Cut the small ray slits first while the wall is strongest, then do the teeth, always sawing away from the narrow bridges.
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8. Barred Eyes, Fourteen Leaves
Big round eyes split by vertical rind bars sit over a button nose and a huge grin packed with square teeth, while clusters of petal shaped leaves fan out from each cheek. Everything is cut through, and the fourteen petals plus the tooth gaps are why this rates hard. Carve from the center of the face outward so the delicate petal clusters are handled last, when the wall is lightest.
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9. Crescent Eyes and Broad Smile
Two upswept crescent eyes squint with joy above an enormous open smile that stretches nearly the full width of the pumpkin, curling up into playful points at each corner. Just three cut-through openings make the whole face, with no nose, teeth, or fragile bits anywhere. This easy design is pure beginner fun; carve the big smile first while the wall is strongest, then the two eye crescents, angling your blade slightly outward so the pieces push free cleanly.
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10. Oval Eyes and Crescent Cheeks
This delighted face beams with two big oval eyes, a small triangle nose, crescent-shaped cheek accents, and an open grin showing a pair of stubby teeth, all dusted with tiny freckle holes. Every shape is pierced through, with the teeth left attached to the upper lip. Cut the delicate crescent cheeks with the tip of your saw only, since their thin curves are the easiest pieces to crack.
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11. Oval Eyes and Round Cheeks
Two big oval eyes glow above a tiny curved smile, with a small round blush circle on each cheek that lights up like a bashful glow. All five features are pierced through, and the shapes are large and simple, making this one of the sweetest easy carves for kids to help with. Cut the little smile last with a fine blade, since that short curve is the only delicate stroke in the whole design.
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12. Round and Square Eyes
A goofy lopsided face with one big round eye and one square eye, a small triangle nose, and a huge open smile interrupted by two buck teeth hanging from the upper lip. All shapes are cut fully through, and the mismatched eyes do all the comedic work. An easy, forgiving carve for kids and beginners; cut the smile last and leave the two tooth tabs of rind attached so they dangle into the glow.
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13. Oval Eyes and Eight Cheek Dots
Big oval eyes sit under arched brows above a round button nose and a broad smile showing four blunt square teeth, with four freckle dots sprinkled on each cheek. The eyes, brows, nose, mouth, and dots are pierced through while the tooth bridges stay connected. Poke the eight small cheek dots first, then cut the large features, leaving the tooth bars until the end so they keep support.
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14. Round and Triangle Goofy Eyes
One round eye and one sideways triangle eye give this pumpkin its delightfully goofy, mid-wink expression, finished with a huge upswept smile and two square teeth hanging from the upper lip. All shapes cut straight through for a bright, cartoonish glow. It is an easy crowd-pleaser; cut around each square tooth carefully, since they stay attached to the top of the mouth, and round off the smile's corners for extra charm.
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15. Tall Eyes and Crooked Tooth
Two tall rounded eyes of slightly different sizes sit high on the pumpkin above a small off center smile holding one square tooth. Only three openings get cut, which keeps this easy pattern quick and friendly rather than frightening. Leave the little tooth attached by carving carefully around it inside the mouth opening, and save the smaller eye for last while your blade is warmed up.
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16. Star Eyes and Six Freckles
This starstruck face beams with two five-pointed stars for eyes, curved brows arching above them, a wide open grin with tiny teeth, and three round freckles dotting each cheek. All the features are pierced through the wall, and the star eyes are the showpieces. Cut each star from its center out to the points, and drill the six freckles with a small round bit for perfectly matched circles.
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17. Lovestruck Heart Eyes Face
This lovestruck face beams with two big heart-shaped eyes under curved brows, a wide open smile showing three square teeth, and playful dot dimples on each cheek. All the features are cut through the wall, so the hearts glow brightest and instantly read as the classic heart-eyes expression. Cut the notch at the top of each heart carefully with short strokes, since that little dip is what makes the shape.
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18. 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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19. 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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20. Arched Eyes and Six Freckles
A vintage-style pumpkin face with tall arched eyes, a triangle nose, a gap-toothed smile, and six little freckle holes dotted across the cheeks. The eyes, nose, mouth, and freckles all cut through, and each eye keeps a rooted pupil tab attached at the bottom for old-fashioned character. Drill or poke the freckles first with a small round tool, and cut toward each pupil tab's base so those thin anchors survive.
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21. Kitten with Long Whiskers
A sweet kitten face with pointed ear triangles, big almond eyes, a small triangle nose, extra-long whisker slits sweeping from each cheek, and a dainty curled smile beneath. All features are pierced through, and the long thin whiskers are what nudge this to medium difficulty. Cut each whisker as one smooth continuous stroke rather than sawing back and forth, and the slits will glow as fine clean lines.
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22. Almond Eyes and Wide Cat Smile
A sly cat face with two swooping almond eyes, a small triangle nose, and an enormous curling grin that stretches nearly ear to ear. The eyes, nose, and mouth are cut fully through, and the thin rind strips inside the smile create the mischievous cat-lip curves. At medium difficulty, the tapering eye points need patience; finish each point with a short pull cut toward the corner.
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23. Crescent Eyes and Curved Smile
Pure cheer: two upturned crescent eyes squint with delight above a huge toothless smile that curls up at both corners. All three shapes are pierced through so the whole face beams with candlelight, and the matching curves give it a warm, laughing character. This easy pattern rewards smooth cutting; saw each crescent in one steady motion following the curve, and round off the smile's corners rather than leaving sharp points.
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24. Unequal Eyes and Opposed Teeth
A lovably lopsided face: one huge round eye beside one small one, over a wide wavy smile with a single square tooth poking down and another poking up from opposite sides. Every shape is a cut-through, and the deliberate asymmetry is the whole joke. This easy design forgives wobbly lines since crooked only makes it funnier; just keep the two teeth attached by cutting around them, not across their bases.
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25. Wide Grin and One Broad Tooth
Made for short, squat pumpkins, this goofy face pairs two upswept triangle eyes with an enormous grin interrupted by a single broad tooth hanging from the top lip. The eyes and mouth are cut through, and the tooth is simply a block of shell left in place inside the smile opening. Cut around the tooth carefully on both sides before removing the mouth pieces so it stays firmly attached.
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