UPDATE – The link no longer goes to the punkinhead font go to this one – http://www.dafont.com/en/voir.php?libelle=Punkinhead insteaf.

punkinhead font

Hooray For Sjohn and Cumberland! –

Punkinhead is a dingbat font of Jack-O-Lantern faces, but it’s more
than just dingbats: Go into WordPad (or any comparable program) and set
the paper to portrait, print a single character from this font on
it in the biggest size that fits (often 600ish points) and voila!
You’ve got a Jack-O-Lantern template (or a really cheap, cheesy paper mask).
I doodled these up at Ruta Maya on a writing break, eager to once again
pervert the humble font into doing something unusual.

Punkinhead has 26 designs (a-z) with mirror (reverse) versions mapped
to the capitals (A-Z). When making your punkinhead, follow these guidelines
for better results:

• Select a pumpkin that will rest easily on a flat surface, and one that’s
  free of bruises or broken bits. Any size will do.
• Print the template lightly; don’t waste printer ink or toner on solid
  black. Convince your printer it’s printing in cyan and you’ll get a really
  light grey that’s still very easy to work with.
• Cover the work area with newspapers. Punkins is messy.
• Cut a clean hexagonal lid, angling the cut inwards to provide support
  for the cap.
• Scoop the insides clean with a rounded scraper, soup spoon, or even
  an ice cream scoop.
• Save the pumpkin seeds as well as the flesh; roast them in the oven
  on a sheet of foil. Add salt and enjoy!
• Place your template over the face of the pumpkin and score (stab little
  dots) along the edges of the design. This will mark the template onto the
  surface of the pumpkin so you can work without paper in the way. Alternately,
  cut the dark part of the template away from the paper with scissors, and
  then use the template as a stencil to mark the design on the pumpkin for
  cutting.
• Long, slender knives or special carving tools work better than bulky
  steak or chef’s knives when doing facial details. Play safe with sharp
  objects! If kids are involved, use plastic safety tools instead of knives.
• Start with the middle of a design (often the nose) and work outward.
  Use gentle, sawing motions. Never hold your knife in the "psycho stab"
  position. Push cut pieces out (or in!) gently with your finger or a plastic
  tool.
• Remember that, depending on climate, a Jack only lasts 2-5 days before
  it gets all saggy and droopy and stinky. You can either accept this, or
  take steps to preserve your punkinhead: Let the punkin air-dry for an hour
  after creating it, then rub it inside and out with a dry, absorbent cloth,
  then coat it with a protectant. There are commercial pumpkin-sealants for
  this purpose, but folks use everything from vaseline to veggie oil to hair
  spray to good effect.
• When you’re ready to light up, use a bit of foil to provide a base
  and anchor for the candle (it can be molded into a sturdy candleholder
  if need be). Some folks also cut a small "chimney" in the lid
  to let excess heat and smoke exit more safely (this also extends the life
  of the punkinhead).