Winking Jack-O-Lantern Pumpkin Face with Cheek Cutouts

Hollow the pumpkin and plan the face

Cut a back lid and scoop the interior to about an inch of wall thickness. Sketch all features with a washable marker before cutting anything: one crescent winking eye on the left, one round open eye on the right, a triangle nose, a three-tooth grinning mouth, and placeholder arcs for the eight cheek holes. Check the arrangement reads as a winking face.

Cut the crescent eye

A crescent eye is an upward-curved arc that reads as a closed or winking eye. Cut the outer arc first, then cut the inner concave arc to meet at both tips, removing the crescent plug. The tips of the crescent are the trickiest points: approach each from one side and finish with a detail knife.

Cut the round eye and triangle nose

Cut the round open eye using a saw or a round spade bit on a drill for a consistent circle. Then cut the small triangle nose. These two cuts complete the upper face before you open the larger mouth area.

Cut the three-tooth mouth

Open the grinning mouth with the three broad teeth rooted in the upper lip. Cut the outer smile boundary first, then cut the gaps between the teeth, leaving each tooth root firmly attached to the lip. Checking that the crescent eye and round eye are at equal heights now helps confirm the mouth is centered.

Add the eight cheek holes

Mark two arcs of four small cutouts each, curving from the nose area outward toward the cheeks. Space them a generous half-inch apart. Cut each small hole individually, using a narrow saw for rounded holes or a punch tool for a more consistent oval or circle. Cutting the cheek holes last means you have a finished face as your reference for placement.

Light and display

Insert a warm LED inside and display the pumpkin so the winking side faces viewers directly. The interplay between the winking crescent and the open round eye reads best when both are visible simultaneously. A warm amber light enhances the cheek hole glow.