Use a pencil to lightly draw on your pumpkin face.
Begin by painting the eyes white and the nose and lips red. Add black accents to the mouth.
Paint a second coat on the eyes, nose, and lips (if needed).Add black pupils and eyelashes.
Now outline the lips and nose in black. You can also add adorable black freckles to the "cheeks".Allow the paint to dry for about 30 minutes.
Step 3: Drill lollipop holes
Use a sharpie to mark where you want to drill holes on the top of the pumpkin.We made our holes 1 - 2 inches apart. Our smaller pie pumpkins had two rows of holes around the stem, while the larger pumpkin had three rows.
Drill through the pumpkin on each of the sharpie marks. We used a 9/64 drill bit but it will depend on the size of your lollipop sticks. See below for more on that.We drilled straight down for the inner holes and on an angle for the outside ring, allowing the lollipops to stick out to the side a bit.Wipe off any pumpkin "guts" that have come out.
Step 4: Add lollipop hair!
This is an optional step, but you can wrap tape around the bottom of the lollipop stick to prevent them from getting soggy.
Now insert the tootsie pops into the holes you've drilled.