10 Homemade Smiling Pumpkin Designs

Explore 10 distinct homemade smiling pumpkin designs 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.
See template →
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.
See template →
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.
See template →
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.
See template →
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.
See template →
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.
See template →
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.
See template →
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.
See template →
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.
See template →
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.
See template →