I have fond childhood memories of chestnuts. My dad would buy a big bag of chestnuts and pour them into the turkey roasting pan, cover the pan, and stick it in a hot oven. When we heard the chestnuts start to explode, we knew they were done! Then we’d each get a plate of them, along with a big glass of milk, and sit at the counter and diligently peel them one by one and stuff them into our mouths. Boy, were they good. And the cold milk was the perfect beverage to wash them down with.
Nowadays I know the importance of puncturing the skin before roasting to avoid those dangerous (and messy) explosions. Poking the skin allows the steam to escape. You can find different advice about the puncturing; the most common is to cut an X into the flat side of the chestnut. Other suggestions include cutting off the tip, simply poking a hole in each side, or cutting the skin all the way around the nut.
Chestnuts can be boiled but after cooking them that way once, I concluded that roasting brings out the nutty flavor better. Some directions say to score, boil, and then roast. And no matter how I’ve scored the skin, there are always some stubborn nuts that refuse to release their skin without a fight. Mold can be a problem too, but if you cook them as soon as possible after buying them, you are not as likely to have a bunch of moldy nuts.
Here is one way to roast chestnuts, and if they are fresh, you will have the best chance of peeling without too much difficulty.
Cut chestnuts along the curved side of the nut with a sharp paring or steak knife. If you can cut a large X or cut all the way around, peeling will be even easier. Try not to cut into the nutmeat.
Heat oven to 350 degrees. Place chestnuts on a roasting pan and bake for 35-40 minutes. Remove from oven, let cool slightly, and peel while still warm. They will be more difficult to peel when cooled completely. Enjoy!