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View all stencils βAbout this stencil
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. This design is rated Intermediate and takes most carvers around 75 minutes from trace to glow. Comfortable knife handling required. Small details and curves.
Pumpkin size guide
- π Small (5β7") β print at 80%
- π Medium (7β10") β print at 100% (recommended)
- π Large (11β13") β print at 130%
- π Giant (14"+) β print at 150% on tabloid paper
Frequently asked questions
Can I resize this stencil?βΎ
Yes. The PDF is vector so it scales cleanly. Print at 100% for a 7β10 inch pumpkin, 130% for 11β13 inch, or 150% for a giant. Use your printer's "Fit to page" or "Custom scale" setting.
What kind of paper works best?βΎ
Standard 20 lb letter or A4 printer paper is fine. Heavier paper is harder to bend around the pumpkin curve. If your printer supports it, set the quality to 'best' so the lines are crisp.
How long will the carved pumpkin last?βΎ
Usually 5β10 days. Coat all cut surfaces with petroleum jelly and store the pumpkin somewhere cool overnight. Avoid direct sun. Battery LED pumpkin lights produce no heat and double the lifespan.
Can I sell pumpkins carved with this stencil?βΎ
Yes, the carved pumpkin you make is yours. The license covers personal and small-scale commercial carving (selling carved pumpkins, photographing them, posting on social). You may not resell the PDF file itself.
What if my printer doesn't print the whole stencil?βΎ
Set 'Page scaling' to 'Fit' in the print dialog and uncheck 'Auto-rotate'. If it still cuts off, the design includes 0.25" of safe-area margin so a small crop won't ruin it.
How to carve this stencil
- 1Print it
Download the PDF and print at 100% scale on letter or A4 paper.
- 2Prep the pumpkin
Cut the lid at an angle, scoop the guts, thin the wall to ~1 inch.
- 3Tape it on
Snip darts in the paper so it lies flat against the curve.
- 4Transfer the design
Poke along every line β about one dot every 1/8 inch.
- 5Carve it
Connect the dots with short straight cuts. Center first, work outward.
- 6Light it up
Drop in a battery LED pumpkin light and you're done.
Tools you'll need
For a intermediate carve like this you'll want a x-acto knife, poker tool, ribbon scoop, and painter's tape. Here's the kit we reach for β start with whatever you already own.

Elmchee Pumpkin Carving Kit
13-piece kit with carrying case
Saws for the larger cutouts, plus a scoop for hollowing. Covers both jobs in one kit.
View on Amazon β
HOME MOST LED Pumpkin Lights
4-pack, battery operated, with remote + timer
Orange glow made for jack-o'-lanterns. The remote and timer light the pumpkin every evening without reaching inside.
View on Amazon β
Speedball 4131 Lino Cutter Set
Handle + 5 interchangeable cutters
Interchangeable cutters for peeling and shading the face. Useful for the finer details.
View on Amazon β
Community Pumpkin Carving Ideas
Carving ideas that use stencils like this one.
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Two round eyes sit above a broad crescent smile that sweeps almost the full width of the pumpkin, making the friendliest face on the block. All three shapes are simple cut-throughs with no fragile pieces anywhere. It is a perfect first carve: drill or poke start holes in each eye, saw the circles smooth, then cut the long mouth curve in one relaxed pass, keeping the crescent's pointed corners crisp.
Beginner-friendlyCrescent Wink and Two Teeth
A playful winking face with one big round open eye, one crescent-shaped winking eye, and a broad open smile showing two square teeth. All the features are simple pierced openings with plenty of solid pumpkin between them, so the face is sturdy and beginner friendly. For this easy carve, cut the large smile first while the wall is strongest, then finish with the crescent wink, angling your blade slightly outward for a clean curve.
Beginner-friendlyRound Eyes and Heart Cheeks
A kawaii-style face made of two big round eyes, a gentle crescent smile, and a glowing heart on each cheek like a blush. All five shapes cut cleanly through the wall, and their simple outlines make this one of the easiest patterns in the collection. Start each heart at its top notch and cut down both lobes toward the point so the little cheeks come out in one neat piece.
Beginner-friendlyFive-Point Star Eyes and Smile
A star-struck emoji face with two big five-point stars for eyes and a broad crescent smile beneath them. All three shapes are pierced completely through, so the stars and grin beam like the real starry-eyed emoji. It is an easy carve overall, with the star points as the only fiddly spots; poke a pilot hole in the center of each star and cut outward toward every point.
Beginner-friendlyUnequal Heart Eyes and Smile
Inspired by the heart-eyes emoji, this lovable face pairs two big heart-shaped eyes with a broad crescent smile. All three openings are cut fully through, so the hearts beam bright pink-orange light after dark. The gentle notch at the top of each heart is the only fiddly spot in this easy carve; poke a starter hole in the middle of each heart and saw up into the notch from inside so the point stays sharp.
IntermediateWink 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.






