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Once you have the right pumpkin, you"ll need the right carving tools for success.
Scooper
Forget the old-school method of using a spoon; craft stores and supermarkets (and even many pumpkin patches!) sell sturdy plastic scoopers that will make the unpleasant job of gutting the pumpkin much easier.
A trick to easy carving is to pick the side of the pumpkin you want to carve and use the scraper to scrape down the skin of the pumpkin so its much thinner. This will allow you to carve quickly and easily since you dont have to cut through thick skin.
Carving Tool
For the actual carving, dont use a knife - kitchen knives are too sharp and dangerous, and silverware knives are too dull and clumsy. As with the scooper, pick up a carving tool at the store - its a thin, small serrated blade attached to a plastic handle.
The small blade lets you go wild with the details and the serrated blade cuts the pumpkin easily.
Having the correct carving tools is half the battle. Choosing what to carve is the other half!
Make Stencils
Go online and find Halloween shapes you like: Scary faces, a cat, a witch hat, candy corn, etc. All you have to do is print the image out ona single sheet of paper and enlarge to the size you'd like it to be on the pumpkin.
Connect the Dots
Then, tape the sheet of paper into place on the face of the pumpkin. Using a knitting needle or metal skewer, poke small holes along the lines of the drawing so it leaves behind a dotted line of the picture on the pumpkin.
Finally, carve out the pieces using your little carving tool. Voila! You have an impressive pumpkin.