One of my favorite Christmas cookies, from my childhood, were the Candy Cane Cookies my Mom used to make. They are still one of my favorite cookies and my Mom still makes sure that I get some every Christmas whether I make it home or not. My wife has learned to make them also. Not that I’m not capable of making them, but they are a labor of love and can be a pain to make. Just another reason that my wife rocks!

So what is so difficult about making these Candy Cane Cookies? Well, first you need to make 2 batches of the dough. One you leave plain, while the other you tint red. You then allow the doughs to chill briefly. Once that’s done you then start rolling out 6-8″ long ropes of dough about 1/4″ in diameter. Taking 1 red rope and one white rope you twist the 2 together and form into a candy cane. These then get baked. And if this sounds like a pain, well it’s even more of pain than it sounds, but they make great looking cookies.

While I loved these cookies as a kid (and still do) I always thought it was strange that they looked like candy canes but they didn’t really taste like candy canes (except for the crushed candy canes that were sprinkled onto the hot cookies, as they came out of the oven). It wasn’t until I was older that I learned that the flavoring for these cookies was actually almond extract. Since I’ve been out on my own, I’ve tried replacing the almond extract with peppermint extract to make these cookies more “candy cane” like, but found that I didn’t care for them as much. I’m not sure if that is due to my bias for the cookies of my youth or if the almond extract really does work better. But I have to admit there is something wonderful in the play of flavors between the almond flavored cookie and the crushed candy canes on top.

Getting ready for the recent bake sale I was involved in, I knew that I wanted to do these cookies, but seeing as it was a bake sale and these cookies were going to be transported numerous times I wanted a cookie what wasn’t as fragile as the candy canes that we usually made. Keeping with the candy theme though I decided to roll the 2 colored doughs into a pinwheel, slice them and bake them with lollipop sticks to create cookie lollipops. And I have to admit I almost like them better than the traditional candy canes. I said almost, but not quite. Again though that is just a bias for the cookies of my youth. Either way you decide to make them they will turn out great. I hope you enjoy them as much as I do

Pinwheel Cookie Lollipops
makes approximately 30-34 cookies

1 cup butter, softened
1 cup powdered sugar
1 egg
1 1/2 tsp. almond extract
1 tsp. vanilla extract
2 1/2 cups flour
1/2 tsp. salt
1/4 cup candy canes, crushed
1/4 cup granulated sugar

In a mixer beat together the butter and the sugar. Add the egg and extracts and mix to combine. Add the flour and salt and mix until a sticky dough forms. Wrap dough in plastic and allow to chill for 45-60 minutes. Meanwhile make another batch of the dough, tinting this one red. Chill this dough also. Once chilled place the white dough on a piece of wax paper and roll out to a rectangle about 15″ inches long and 11″ wide. Adding only enough flour to keep the dough from sticking. Do the same to the red dough but only rolling it out to 15″x10″. Center the red dough on top of the white dough and gently roll up pinwheel style along the longer edge, rolling as tightly as you can. Transfer roll to a large piece of plastic wrap and wrap the dough tightly, twisting in the ends a bit to tighten the dough and give you a uniform width throughout. Chill the dough overnight.

Preheat your oven to 375°F. Trim one end off of the cookie roll and start cutting slices about 1/4″ thick. Remove the plastic wrap from the individual slices (it’s easier to slice it with the plastic on it).

Use a thin bladed slicing knife and wipe it clean every couple of cuts for ease of cutting. Place slices on parchment on cookie sheets and add lollipop sticks (if using). Bake for 9 minutes. Meanwhile combine the crushed candy canes and granulated sugar. After 9 nine minutes remove cookies from oven and lightly sprinkle with the candy cane/sugar mixture. Return to the oven for 1 minute longer (no longer). Remove from oven and allow to cool, on the pans for about 4-5 minutes. Transfer to a cooling rack to continue cooling.