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Start with an average sized, pear shaped pumpkin with thick skin. You need a pumpkin with thick skin because you will be carving away some of the pumpkin's surface. We are carving our pumpkin upside down to match the shape of a skull.
Hold the pumpkin upside-down. Decide where the eyes, nose and mouth will be located. Use a dry-erase marker to outline the two eye sockets, an opening for the nose cavity and a straight line with two crescent shapes on both ends for the mouth. If needed, print a picture of a skull as a reference when drawing the facial features.
Cut the outlines using a carving tool or knife. These holes will serve as reference points when shaping the contours of the skull. For the mouth, just cut a straight line; the teeth will be carved after the skull is shaved and formed.
Use an angle grinder or small sander to remove all of the skin from the pumpkin. You can also use a hand tool, like a vegetable peeler or file but a grinder or sander are quick and effective tools for this step.
Use the same tool to shape the contours of the skull and cheek bones. Use a picture of a skull as a guide for these steps: