I've been carving pumpkins for the past four or five years, and every year they get a little more detailed. This year I decided to take old Civil War-era photographs and give them spooky twists, creating a triptych: "See No Evil, Hear No Evil, See No Evil." This Instructable will take you through the steps I used for See No Evil, but the same steps applied to all of them, and will apply for any intricate or photo-realistic pumpkin you might want to try. I'm including the stencils for all three, in case you want to give these designs a try!

Step 1: Choose Your Design and Create Your Stencil

For this pumpkin, I used a Matthew Brady photo of a Civil War-era politician that I found on the National Archives Flickr page, but you can use any photo or image you want. I Autodesk SketchBook on a tablet to draw lines over the contours of the face in a layer on top of the photograph (you could use any photo editing software for this); I use solid lines for clearly delineated areas of light & dark, and dotted lines for more subtle transitions of shading. In this case, I also left out the man's eyes, and added veins coming out of them. Once I trace over the photograph, I isolate the layer with the stencil and print it out onto a piece of 8.5x11" paper.

This was actually the first year that I made the stencil digitally - in the past, I simply printed the photo and traced the stencil over it with a sharpie. That works too!

Step 2: Get Your Tools Ready

To stencil and carve, you'll want a few things on hand:

A pumpkin
Saral transfer paper (available in many art supply stores, or online)
Fixatif spray (available in pretty much any art supply store)
Ballpoint pen
Permanent marker
Linoleum cutter
X-acto knife
Pottery loop tools - one double-sided small tool, one larger tool
Any other handy tools you might have - I like to use dentist picks, wax carving tools, pottery needle, screwdrivers, pocket knives, etc, pretty much anything that can cut a pumpkin
Knife (to cut the back out of the pumpkin)
Latex gloves (optional)
Small camping lantern (or other light source)

Step 3: Apply the Stencil to the Pumpkin

TOOLS:

Saral transfer paper
Fixatif spray
Stencil
Ballpoint Pen
Tape

Choose your pumpkin carefully - you want to look for one that has as smooth and flat a surface as possible. Wipe it off with a damp paper towel and dry it before applying the stencil, you don't want any dirt from the pumpkin patch getting in the way!

Tape a sheet of transfer paper to the pumpkin - make sure the side with the dusty transfer material is facing the pumpkin - and tape it as flat as possible. It can be tricky to put a flat paper on a round object, so fold and crease the paper as necessary (see photo).

Next, do the same with your stencil. Once it's taped on top of the transfer paper, draw over the entire stencil with a ballpoint pen. When finished, carefully remove the tape and paper, and your stencil should now be on the pumpkin!

Take the pumpkin outside and spray it with the fixatif, and let it dry for at least 30 minutes. The fixatif will help the stencil adhere to the pumpkin, and keep it from rubbing off as you carve.

Step 4: Start to Carve!

TOOLS:

Permanent marker
Linoleum cutter

Using your permanent marker, fill in the absolute darkest areas of the design - these will stay uncarved. Any areas of the pumpkin that you want to keep dark that aren't the absolute darkest spots can also be left uncarved, but don't use the marker.

Then, use your linoleum cutter to cut out layers on the rest of the pumpkin. Remember, the deeper you carve, the lighter that area will be! At this point, don't worry too much about being exact - at this stage you just want to get a general approximation of the light/dark levels. You can finesse it at the next stage, once you actually hollow out the pumpkin and see how it looks with a light inside.

Step 5: Optional Step: Take a Break

At this point, you've probably been working for a couple of hours. If you want to finish later, even the next day, just take some plastic wrap and tape it over the carving. It'll keep just fine overnight. Have a snack, grab a drink, get a good night's sleep - you've got more work to do!

Step 6: Hollow Out the Pumpkin

TOOLS:

Knife
Pottery loop tool (large)

This is one of the best tips for pumpkin carving: cut out the back of the pumpkin, not the top. It will make it a lot easier to hollow out and light the pumpkin. Cut a square in the back, and pull out the guts and seeds with your hand or a spoon (I like to use a latex glove for this part!). Then use your pottery loop tool to scrape away the wall of the pumpkin behind your design. Your pumpkin will likely be 2-3 inches thick, and you can scrape away most of that - the more you scrape from the inside, the brighter the design will be when lit. Another thing to keep in mind is the more you take from the inside, the less you need to take from the outside. If you hollow the pumpkin until it's quite thin, you can carve less deeply on the outside, giving you more precision in your design.

Step 7: Light It Up, and Keep Carving

TOOLS:

lantern (or other light source)
linoleum cutter
pottery loop tool

Turn off the lights & turn on your small lantern. Put it in the pumpkin, and continue carving in the dark. Scrape away more of the pumpkin from the areas that need to be lighter - I find that using the linoleum cutter will allow you to work quickly and precisely, and you can then use the double-sided loop tool to scrape a bit more and smooth out the harder edged lines of the linoleum cutter. The photos above show the progression of the pumpkin from when I first put the lantern in, to the finished product. Keep going until your pumpkin looks finished! This can take a couple hours, depending on how much of a perfectionist you are.

Step 8: Appreciate & Refrigerate!

Congratulations, you're done! Step back, wipe the pumpkin gunk off your hands, and admire your handiwork. If you want to keep the pumpkin for more than a couple of days, I recommend storing it in the refrigerator. It's great for preserving it, and for freaking out any guests at your house who are looking for a cold drink. Enjoy!