Step 1
Usually, when we draw a pumpkin, we think “round”, so we might start out with a circle.

Step 2
This is a pretty good start, and people usually get what we’re drawing. It’s not wrong, since every pumpkin is different…

Step 3
But because it’s completely round, it looks like a ball, and it’s going to roll all over the place.

Step 4
Most pumpkins you see have at least a little bit of a flat base. The bigger they get, a lot of times gravity affects them to make them this way—flatter on the bottom. I’m also giving it a little bit of a flat top.

Step 5
All pumpkins are indeed shaped different. Some are really round, some are kind of lantern-shaped, some are really odd and lopsided. But, they are all pretty much round-ish. Mine will be sort of bottom-heavy: larger at the bottom than at the top.

Step 6
Imagine a line going down the center of your pumpkin. Then, draw the segments from the top to the bottom, but not in the middle. The closer you are to the center, the closer to straight the line will be, and the further out, the more the lines will look like the outside curve.

Step 7
Now, draw the stem. Pumpkins grow on vines, so the stem is usually a little wider at the pumpkin end. Also, make it a little curved and twisted to give it a natural look.

Step 8
Draw the basic shape of the face. You can have whatever look you want, but I’m going for a more common face.

Step 9
Draw in the teeth or pupils for the eyes if you want, then erase away the lines you don’t want to use or go over everything darker for your final picture.

Step 10
Now you can round out the segments at the top and bottom, add the cut for the top hole, and generally finish the whole thing off. I usually don’t like to let the segment lines touch the cut out parts. It distracts when they touch, but your eye fills it in if you choose not to.