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Adapted from Gourmet
You will need either a silicone baking liner or parchment paper to line the cookie sheets and prevent the candy from sticking. I learned this the hard way!
Makes about 3 dozen cookies (the number will vary depending on the size of the cookie cutters)
1 hour preparation time, plus 2 or more hours to chill the dough
Approximately 1 hour baking time
2 1/2 cups flour
3/4 teaspoon salt
1 1/2 sticks (12 tablespoons) butter
1 cup sugar
1 egg
1 teaspoon vanilla
Assorted colors of hard candy (Life Savers work well)
In a medium bowl, whisk together the flour and salt. In a mixing bowl, mix the butter and sugar together at medium-high speed. Scraping down the sides once or twice, beat the mixture until it lightens in color and is light and fluffy, about 3 minutes.
Mix in the egg and vanilla. Add the flour mixture and beat until just combined. Divide the dough into 3 batches. Place a batch of dough on a sheet of plastic wrap and flatten it until it is about 5 inches in diameter. Wrap the plastic wrap tightly aroung it. Repeat for the other two batches. Refrigerate the dough for at least two hours.
To prepare the candies, separate them by color into sturdy baggies. One at a time, wrap the bags in a kitchen towel and smash them with a hammer. The children will definitely want to help with this part. It doesn't matter how small the candies get because they will melt together when the cookies are baked. So let the kids go to town. Put the candies in separate bowls by color.
When you are ready to bake the cookies, place a baking rack in the middle of the oven and preheat the oven to 350 degrees. Place a silicone baking liner on a cookie sheet.
Remove one batch of dough and roll it out on a well-floured surface. Cut as many large shapes as you can out of the dough. Using a spatula, carefully transfer the cookies to the cookie sheet. With a smaller cookie cutter, cut a small shape out of the center of the cookie. Sprinkle about 1/2 teaspoon of crushed candy into the opening (the amount that you need will depend on the size of the cutter you use). If you would like to use the cookie as an ornament, use a straw to cut a hole in the top.
Bake the cookies until their edges are lightly golden, about 10-12 minutes. Transfer the baking sheet to a cooling rack and allow the cookies to cool.
Roll the dough scraps into a ball, and roll them out again. If the dough is too soft, flatten it into a disk, and put it into the refrigerator to chill for 15 or so minutes before you use it again.
Repeat the process with the remaining dough until you have baked all of the cookies. Gourmet says to reroll the scraps only once, but I think you can keep going until you are out of dough. The dough may not hold together as well, but my kids have never turned up their noses at the later batches. If you are making some cookies as ornaments, you may want to use the earlier batches.
Store the cookies in an airtight container between sheets of wax paper for several days.