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🎃9 designs · Updated for 2026

Intermediate Smiling Pumpkin Designs

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

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9 intermediate smiling pumpkin designs

Pick a favorite, hit print, and you'll have a glowing porch by sundown.

Intermediate

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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Intermediate

Brows and Six Cheek Dots

A classic jack-o'-lantern face with slanted triangle eyes topped by separate angled brow cuts, a diamond nose, and a wide grin broken by six blocky teeth, plus three small round holes dotting each cheek. Every element is cut fully through so the whole face blazes at night. A solid medium project; drill or punch the cheek dots first while the wall is strongest, then saw the eyes, brows, and mouth.

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Intermediate

Arched Eyes and Seven Slots

This cheerful face pairs tall arched eyes, each with a round pupil left attached at the top, with a triangle nose and a huge grin broken by seven tooth slots. The eyes, nose, and mouth are pierced while the pupils and tooth bars remain as connected shell. The attached pupils are the trickiest part, so cut around each one carefully and leave a generous bridge so they stay anchored.

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Intermediate

Arched Brows and Single Tooth

A wholesome grinning face with arched eyebrows, round eyes that keep their pupils as uncut dots, a small triangle nose, and a big open smile showing two square teeth. The brows, eye rings, nose, and mouth are pierced through while the pupils and teeth remain as attached pumpkin. Cut the eyes slowly so each floating pupil keeps a solid connecting bridge to the shell.

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Intermediate

Round Pupils and Five Teeth

A big-eyed, grinning jack-o'-lantern face with round pupil tabs left inside each eye and five square teeth breaking up a wide smile. The eyes and mouth are cut clean through while the pupils and teeth remain attached to the rind as solid bridges. Those round pupils make this a medium carve, so pierce a relief hole beside each one first and saw toward it rather than levering the blade, which can snap the connecting tab.

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Intermediate

Eight-Bridge Circular Smile

A big circular smiley face beams from the pumpkin, drawn with a segmented ring outline, two oval eyes, and a wide upturned smile with curled corners. The ring, eyes, and mouth are all cut through, while small bridges break the circle into sections that keep the face anchored to the shell. Leave every bridge intact until the end so the outline ring stays firmly attached.

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Intermediate

Heart Eyes and Three Teeth

Two big heart shaped eyes with curling lash accents beam above a small triangle nose and a wide grin broken by three square teeth. Every shape is cut all the way through, so candlelight pours out of the hearts and the toothy smile. Take the lash flicks slowly with a fine saw, since those narrow tips are the only fiddly part of this medium design.

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Intermediate

Happy Crescent-Eyed Grin

A cheerful jack-o'-lantern face with sweeping crescent eyes, a small notched nose, and a wide grin framed by two pointed fangs and blocky lower teeth. Every feature is cut fully through so the whole face glows. The crescent eyes taper to fine points, so use a thin saw and cut toward the tips from both directions to keep the corners crisp.

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Intermediate

Leaf-Eyed Smile

A grinning jack-o'-lantern face where both eyes are replaced by seven-fingered cannabis leaves, paired with a small triangle nose and a wide smile broken up by blocky square teeth. The leaves, nose, and mouth are all cut through so candlelight pours out of every shape. The leaf points are narrow, so at medium difficulty use a fine saw and cut each finger from the tip inward to keep the serrated edges crisp.

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Frequently asked

Are these pumpkin designs free to download?+

Yes — every pumpkin design on this page is free. Click the preview to download the PDF.

Do I need special tools to carve these?+

A basic carving kit with a serrated saw, a poker, and a scoop covers 95% of pumpkin designs. Detailed designs benefit from an X-Acto knife.

Can kids use these pumpkin designs?+

Designs marked Easy or Kids are great for younger carvers with adult supervision. Plastic carving tools are safest.

Intermediate Smiling Pumpkin Designs

100% free

Print-ready PDF

Carve tonight

9 intermediate smiling pumpkin designs

Round-Eyed Clown With Brows

Brows and Six Cheek Dots

Arched Eyes and Seven Slots

Arched Brows and Single Tooth

Round Pupils and Five Teeth

Eight-Bridge Circular Smile

Heart Eyes and Three Teeth

Happy Crescent-Eyed Grin

Leaf-Eyed Smile

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