My local pumpkin patch sells not only pumpkins and squash during the fall season, they also have mountains of dried gourds in a variety of shaped and sizes. These gourds cost from 75 cents to 7 dollars each.
So back in October I filled my wheelbarrow with a pumpkin or two and a slew of gourds for painting. Gourds may be spherical, peanut-shaped, pointy, etc. I try to choose a variety of shapes and sizes. Pick up a gourd and look at it. Does its shape suggest anything? A snowman, Santa, elf? Maybe a jack-o-lantern, a piece of fruit, or a bird.

Make sure the gourd is sound - no cracks or holes. I've been told that generally a gourd with lots of seeds inside has thicker, stronger walls. If it's going to need to stand up, make sure that it does. (You may want to make some hanging ones, too. The crook-necked ones are great for that.) Sometimes a wobbler can be sanded a bit on the bottom to stand better. Sometimes you just need to shake it and move the seeds inside to make it stand up.

Step 1: Clean the Gourds

The gourds have been outdoors drying for a year or so. They are gray and dirty.
Once I get them home, I brush them off, then sand with 150 grit, or whatever sandpaper I have on hand. Then I give them a good rubdown to remove loose dirt and sanding residue.

Step 2: Time to Paint

Now it's time to paint. As I generally need to look at something to be able to paint it, I look for designs in store ads, on Christmas cards, even holiday paper plates and napkins.

Usually the shape of the gourd dictates the figure you'll create.
Where will the face go? Will it need a hat or cap? I used acrylic craft paints from the craft store. They generally go on smoothly and cover well in one coat (except white). Gloss paint looks really good on the finished gourd, but can cost twice as much as flat paint. Paint the background or base coat first. Then smaller areas like the face, hands, beard, or hat. Details last.

Step 3: Finish Coat

Gourds will last longer and wear better with a clear top coat, especially if you plan to display them outdoors. If you didn't use gloss paint, add a coat of clear polyurethane. You can use a spray or brush it on. Do this step in a well-ventilated area, as it can get stinky.

Step 4: Finishing Touches

Does your gourd need finishing touches? Usually, I paint on hats, gloves, caps, scarves. But you can make accessories to add for a more 3-d look. I made hats for snowmen by cutting out 2 circles and a strip of stiff felt, and gluing them together. Or, earmuffs can be comfy. Two pompoms and a pipe cleaner glued on can make a set. I could even see adding stick arms to a snowman. I suppose you'd need the right tool to drill into the gourd without cracking it, and I don't have such a tool.