Preparing The Pumpkin
Wash and dry your pumpkin thoroughly before starting. After printing your pattern, use scissors to trim off the excess paper around the design. Choose the smoothest side of the pumpkin (typically the side it wasn't laying on while growing) and place the pattern over it.

Pleating The Pattern
If you're having trouble getting the pattern to lay flat, you can pleat the pattern (or cut slits) in areas that don't detract from the overall image. This slight bit of overlapping paper with help the pattern curve over the rounded surface of the pumpkin.

Taping Down The Pattern
Once it's laying flat, tape the pattern securely around all the edges. Scotch tape or masking tape work well. If you had your pumpkin outside, you may want to let it get to room temperature first. Tape often has trouble sticking to cold pumpkin skin.

Transferring By Transfer Paper
Transfer Paper is probably the fastest and easiest way to trace a pattern onto pumpkin skin. Before taping down the paper pattern, first tape the transfer paper to the pumpkin (with the darker side facing toward the pumpkin, of course) and then tape the pattern over that. Like carbon paper, you can transfer the pattern by tracing over the lines with a pencil or ballpoint pen.

Transferring By Poking
Use the poking tool or a push pin to lightly poke holes along the lines of the pattern. You don't need to go deep, just make sure to break the surface of the paper and the pumpkin's outer skin. Depending on the level of detail needed, make your holes 1/8 to 1/4 inch apart.

Transferring By Pounce Wheel
Some carving kits come with a pounce wheel, or you can buy a nice metal one separately. At the end of the handle is a spiked wheel, which you can roll along the lines of your pattern. While not ideal for sharp turns and extreme details, the wheel can make quick work of long lines and gradual curves.

Making The Poked Dots Visible
When you're sure you've poked along every line, remove the pattern and save it for carving reference. Working under bright light will help you see the little holes better. If you really have trouble seeing the dots, you can rub flour over the design to turn the dots white. To make following the lines really easy, connect the dots with a fine point permanent marker (like a Sharpie).

Rechecking The Thickness
After your pattern is transferred, this is a good time to make sure your pumpkin is the right thickness in the area you're about to carve. Stick one of the carving saws through an area of the design that you know will be a cut out hole (you don't want these depth test holes to show in your final design). Push the saw through until you see or feel it come through the inside. Pinch the saw on the outside, right against the surface of the pumpkin, and pull it out. The saw should have only gone in an inch or so. You can check the depth this way in a few areas to make sure you have an even thickness behind your whole design.