My pumpkin family is about twenty years old. They were such a simple yet fun project to do.
My dad cut me a log and then here are the steps:
I de-barked the log (not an easy thing to do) basically by roughly cutting and then sanding the post.
Then I cut it into sections with a chain saw. I made the sections all different sizes.
Now for orange OUTDOOR acrylic paint - several coats.
Drill a hole in the top and glue in a dowel you painted green.
Draw and paint faces once again using OUTDOOR paint.
And you are done. Every year they will weather a bit more and you will find that everyone loves these permanent jack-o-lanterns.
A little story about my pumpkin family:
You will see from the photo that there are nine left in my little group. There once were twelve. I gave one to my daughter for her own front step when my grandson was tiny.
The other two kind of walked away. About ten years ago, a little boy stopped by my home a week or so before Halloween, rang the bell and asked if he could have one. How could I say "no"? And then a few years ago, a little boy was trick-or-treating and when he was leaving, he just picked up the littlest one I had. His dad told him to put it down and he started to sob. As a result, that pumpkin found a new home.
Just like in a real family, apparently my pumpkins sometimes feel the need to leave the nest.