The large pumpkin should be at least 3 times bigger than the small pumpkin.
Trace a circle in the mouth area where the small pumpkin will sit. Make the circle a bit smaller than the pumpkin (better to make the hole too small than too big.)
Use a small hand saw or knife to cut out the traced circle making sure that the hole is smaller than the widest part of the small pumpkin. Then gradually increase the size of the hole by shaving thin layers from the sides until the pumpkin fits snuggly.
Draw a face on the large pumpkin. Start with the mouth around the small pumpkin hole. The hole should sit somewhere within the mouth (ours is off to one side). Draw the rest of the face (we choose to make our pumpkin winking).
Before carving the facial features, plan which pieces will be removed completely and those that will be partially shaved as a 3-dimensional detail. On our pumpkin, we shaved the teeth and discarded the space in between them. When cutting the mouth, avoid cutting the top and bottom of the small pumpkin hole; leave as much of this space untouched as possible. For the open eye, we removed the white and left the iris behind. Cut along the edges of the pieces that will be left behind and discard the pieces that get cut out.
Use a razor blade or electric rotary tool to shave the 3-dimensional details. The depth you’ll shave for this step will depend on the thickness of the pumpkin. Leave behind at least half the width of the pumpkin’s wall to ensure that the shaved pieces are strong enough to stand on their own. Shave about a 1/4 inch from the teeth, leaving a slightly elevated ridge at the top of each tooth to form the gums. Shave the iris of the eye and any other 3-dimensional details you wish to include.
Remove the bottom of the small pumpkin and gut it. Use a dry-erase marker to sketch a frightened face then use a knife to cut it out.
Fit the small pumpkin into the hole by gently wiggling it up and down until it fits. Avoid any side to side motion which could break a tooth. Tooth picks can be used to reinforce the positioning of the pumpkins as well as any broken pieces.
This project was designed and sculpted by Tom Nardone, founder of www.ExtremePumpkins.com and author of the national bestseller, Extreme Pumpkins.