The last couple years I have fallen in love with carving pumpkins. Its easy to work with, and cheap enough to not make a guy cry if you mess up. I started with the pumpkin carving kits, which I still use a lot.
When I wanted to try my hand at shading and adding depth to pumpkins I needed a different tool. I started by trying my wood carving tools. This worked, but was slow and tedious work. In comes the Dremel tool. Its easy to use, not horribly loud, and makes quick work of turning the pumpkin into mush.
I REALLY wanted to do this 2 weeks ago, but the pumpkins just don't last that long with out getting saggy, mushy, moldy, or a combination of the 3. Hopefully you can make use of this Instructable to make your masterpiece.
Follow along as I try to show the steps I took to make a pumpkin the neighbors will be envious of.
Step 1: Find and draw your pattern
Start simply, with objects that don't have 5 different shading levels. I still have not attempted a real persons face. I'm sure I can, I'm just chicken.
I started with the Instructables.com robot. It's reasonably simple shading wise, but detailed enough to be impressive in the end. The nice thing about shading is you don't HAVE to do it to make it look good, but it does add to the wow factor.
If you can draw halfway decent you can just use a permanent marker to make a pattern right on the pumpkin.
If you can't draw well, print out the design you like, and tape it to the pumpkin. You can use an old ball point pen to make shallow pokes along the paper pattern and go back later and connect the dots.
How ever you do it, have fun. You can't grow your skills, or find new ones, if you don't step outside your comfort zone.