Depending on the type of squash being used, peeling it can be a daunting and even dangerous task. Summer squash tends to have a thin and tender skin, which can easily be removed with a conventional vegetable peeler. Winter squash, however, typically has a thicker and tougher outer skin, which can make removal challenging. Attempting to remove the tough skin with a regular vegetable peeler or paring knife can leave one with sore wrists and bandaged fingers.
There are two basic options when it comes to peeling squash: peel it raw, or cook the vegetable to some degree. Cooking helps make the skin softer and easier to remove. How the squash will be served is usually the deciding factor in choosing which method to use.
Cooking the squash prior to peeling does tenderize the skin, but it can also affect the consistency of the vegetable and may not be suitable if you plan to dice or cut it in a given shape. In this case you will want to peel the squash while it is raw. Start with cutting off the top and bottom and then, if it has a bulbous portion, separate it from the straight part. Stabilizing the squash on its flat end, use a very sharp knife or serrated peeler and begin to remove the skin, cutting down and away from your hand. Another option for peeling raw squash is to cut it into smaller pieces and then, with a knife or peeler, remove the skin.
If peeling the vegetable raw proves too difficult but you don't want to lose the firmness of the flesh, you can cook it very briefly (e.g., less than a minute in the microwave, or for about four to five minutes in boiling water on the stove top) to steam the skin without cooking the flesh. This will make it easier to remove the skin and still allow you to prepare the squash as you wish.
If you plan to use the squash for a base in a recipe where it will be mashed, pureed or are just looking to eat it roasted, the task of peeling the skin is even easier. Simply cut the squash in half and scrape out the seeds. Place the cut sides up on a baking sheet and bake at 350°F (176.6°C) for 45 minutes. Allow it to cool and then scoop the flesh away from the skin.
Lastly, if all else fails, there is always the option of pre cut and peeled variety found in stores. This may save time and effort, and in some cases, it may be the safest option.