This is a pumpkin I carved of me and my fiancee for our wedding. To get a nice final product you need a good pattern. I tried the following method with a few photos until I found one that worked the best. The original source image is this:

The background for this image was very dark, so I decided to cut in a Chicago skyline in the background. The first thing you need to do is remove the color. You can do this with Image->Modifications->Desaturate

Next, in the layers window, add a curves adjustment layer and click OK. You don’t need to change any of the settings at this point.

Now add a Posterize adjustment layer and set the number of levels to 3. This will give you the black, grey, and white areas you need for the pattern.

Now double click on the curves layer to edit it’s settings. Play around with this until you find the most visually appealing settings.

I found certain curves looked good only for a particular part of the image. I ended up doing this in sections, and modifying the underlying image by darkening areas and lightening areas until the pattern looked best. Keep in mind the white areas will be completely cut out, so any grey and black areas will need to be supported somehow. This can call for some more tweaking. After a while I ended up with this pattern.

For carving, print the image the size that fits best on the pumpkin. Tape it to the pumpkin and fold and cut around the pattern until it lays as flat as possible to the skin. Using a pin, poke through the pattern and the pumpkin skin along the lines where white meets black, white meets grey, or grey meets black. Poke enough so you will be able to connect the dots once the pattern is off. It’s probably more than you think.

Cut off the top and scoop the insides, if you’re using a fake pumpkin like I am, you don’t even need to worry about this. If you are scooping, you can use a few pins to guage the thickness of the pumpkin around where your pattern is. About a half in to 3/4 of an inch seems to be a good thickness. The pumpkin carving kits you get at CVS or Walgreens have good scoops and saws. I ended up carving out the white areas first, then doing the mid-tones. For mid-tones I used wood carving tools from Joanne’s Fabrics. I’ve heard of another person who uses a Dremel tool. I will need to try that next time.

The pumpkin doesn’t look great when your carving it or when it’s done, but just follow the lines of your pattern, and you will be ok. Do not follow your instinct here, follow your pattern. You might lop of an ear that doesn’t look right. You’ll see it come to life when you put a light in it. Feel free to carve more after you light it up and find areas that need more work.