10 Toothy Grin Pumpkin Faces

We curated 10 of the very best toothy grin pumpkin faces so you can pick one and start carving in minutes.

1. Long Pupils and Triangle Grin
A mischievous jester face topped with an arcing crown of small diamond cutouts, tall eyes with long slit pupils, diamond accents on each cheek, and a huge grin lined with pointed triangle teeth. Every diamond, eye, and tooth gap is pierced through, so the whole face sparkles like carnival lights. As an expert pattern full of tiny repeated shapes, cut all the small diamonds first with a narrow saw before opening the large mouth, which weakens the wall.
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2. 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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3. 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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4. Hanging Pupils and Eight Bays
An elaborate theatrical face with knowing eyes whose pupils hang from the upper lids, framed by ornate teardrop flourishes across the brow and temples, above a huge grin packed with long individual teeth. Dozens of small cut-through openings build the pattern, with slim rind bridges holding every tooth and swirl in place. Number your openings and remove the smallest flourishes first, saving the big mouth bays for last so the web of bridges keeps its strength.
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5. Double Bars and Zigzag Teeth
An elaborate jack-o'-lantern face built from layered geometry: triangle eyes barred with double rind strips, arched claw-like brows, diamond accents down the cheeks, and a wide zigzag mouth of interlocking teeth flanked by curling flame flourishes. The many openings are cut through around a lattice of thin surviving rind. This expert design demands a sharp fine-tooth saw and a plan: cut from the center outward, finishing the outer flourishes last while the wall is still strong.
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6. Triangle Ring and Jagged Grin
An ornate expert-level face framed by a full ring of small triangle cutouts circling the pumpkin, with chevron-crested brows, barred flame-shaped eyes, a diamond nose, and a huge jagged grin holding fourteen zigzag teeth. Everything pierces through, so the finished lantern sparkles from every angle like carved lace. Plan your order: punch the border triangles first while the wall is rigid, then work inward, saving the long fragile grin for the very end.
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7. Vintage Arches and Round Grin
Arched triple line brows curl above big eyes divided by rind bars, a long triangle nose drops between them, and a huge grin shows a full row of rounded teeth with dotted curlicue accents swirling at each cheek. All the openings are cut through in a cheerful retro style straight off an old holiday postcard. Rated hard for its many small dots and thin brow lines, it rewards a fine detail saw and a drill for the dots.
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8. 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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9. Wrinkled Eyes and Uneven Teeth
A mischievous scowling face with arched eyebrows over round glaring eyes, small wrinkle slits fanning from each eye's outer corner, diamond accents dotting the cheeks, and a sweeping smile packed with uneven square teeth. Every cut pierces through, so light streams from all the details at once. A hard carve where the wrinkle slits are the fussy part; cut those hairline slivers with a detail saw before opening the large eye holes beside them.
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10. Four Teeth and Notched Tongue
Arched brows curve over squinting eyes while a huge open mouth shows four top teeth and a notched tongue lolling below, with short laugh lines radiating from each cheek. The face is all pierced cuts, and it rates hard because the tongue and teeth stay attached by narrow tabs inside the big mouth opening. Cut the mouth outline first, then carefully notch around the tongue tab last so it does not break free.
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