Chocolate Peppermint Pinwheels and Cookie Parties

So our annual cookie party was last week! I baked and I baked and then I baked some more. I think I made more than 30 dozen cookies in total. And then I decorated. And thankfully my sister-in-law had mercy on me and came and helped me decorate.

The key to keeping yourself sane when you’re hosting a party is making lists. I started with a list of the cookies and sweets I wanted to make this year, then I put them in order of least to most time-consuming to help me decide what order to make them in:

magic cookie bars
minty fudge
toffee
chocolate chip cinnamon cookies
pepper cookies
snickerdoodles
red velvet cookies
gingerbread
chocolate peppermint pinwheels
Russian teacakes
pumpkin spice truffles
candy cane cookies

Once I figured out what cookies I wanted to make, I also made a list for decorating. After all, what’s a Christmas party without decorations? I decided on an ornament theme, so I got hung little snowflake ornaments all over the house, filled a vase with ornaments for the cookie table centerpiece, decorated my fridge with ornaments cut out of wrapping paper (because we didn’t have a tree yet…), and made name tags for all the cookies in the shape of ornaments. (Thank you, Kelly, for your mad ornament-cutting skills!)

I got started about a week ahead of time and vowed to cross at least two things off my list each day, be it baking or decorating. My goal was to have everything made by the day before the party so that I could spend the day of cleaning the house for guests. And I almost made it—though I must admit I was frosting gingerbread cookies about half an hour before everyone started to arrive!

Over all, having the lists to rely on was amazing. Nothing slipped through the cracks, and I was still excited to be having the party as I was laying out the table just before our guests arrived. My main failing was in being indecisive about decorations (yeah, that list changed several times during the process), which meant that I spent several days buying and exchanging ribbons and twinkle lights, etc., before I could cross “buy decorations” off my list. But all in all, I would say that if you intend to host a Christmas party, you should make about a thousand lists and plot out a timeline for how to accomplish everything before the big day.

Now. Let’s make some cookies! My husband said these pinwheel cookies were his favorite, and while I still haven’t figured out how to get the chocolate not to crack during baking, they are pretty darn delicious!

Like many Christmas favorites, these cookies start out as sugar cookies and then we embellish. They make a perfect addition to your Christmas cookie array, because they are so pretty and festive!

Cream the butter and sugar. When the mixture is fluffy, add the whole egg, the egg yolk, and milk. Scrape the sides of the bowl and beat again.

Sift together the flour, baking powder, and salt. Mix the flour into the butter mixture. The batter will be stiff, but also a bit sticky. (Sorry, I didn’t take pictures of the sugar cookie dough!)

Now comes the fun part. Melt the unsweetened chocolate in a medium bowl. I microwaved for 1 minute, stirred, and then microwaved another 30 seconds until everything was completely melted. Stir in the vanilla, then add in half of the sugar cookie dough. Using a pressing motion, mash the cookie dough into the chocolate until evenly distributed. Set the chocolate dough aside.

Break about 6 regular-flavor candy canes into chunks (this will probably happen naturally as you peel the wrappers off). Put the pieces into a large plastic bag and seal the bag. Using a rolling pin or a can of soup, or really anything solid and heavy, pound the candy cane pieces into small bits. I don’t recommend using a rolling motion, because the candy shards will pierce the plastic bag and probably escape.

Meanwhile, melt the white chocolate in a small bowl.

Stir the white chocolate and the peppermint crumbs into the remaining sugar cookie dough. Make sure the peppermint is well distributed. If you like peppermint more than I do, you could also add a splash of mint extract to this half of the dough, but I think the mint flavor is distinct enough and not overpowering without the extract. Set the minty dough aside.

Sprinkle one side of your counter or workspace with confectioner’s sugar. Work the chocolate dough into a rounded loaf and then set it on the counter; cover the top with more confectioner’s sugar. Roll out the chocolate dough into a ¼″ thick rectangle.

Repeat on the other side of the counter with the minty dough. Notice that the minty dough is much, much softer than the chocolate dough, so be careful not to rip it.

Very, very carefully roll up the minty dough and transfer it to sit on the chocolate dough. Unroll it, then repair the inevitable gashes by pressing the top dough back together.

Cut the dough lengthwise down the middle, so that there are two very skinny rectangles side by side. Roll each up lengthwise into long, thin logs. While you do this, the chocolate dough will probably crack in several places. This is because a) the melted dark chocolate makes the dough less pliable; and b) it is on the outside, which means it has to stretch more. Try to press the cracked chocolate back together as you roll the doughs up.

Wrap the dough logs in wax paper and refrigerate for 2 hours.

Heat the oven to 375° and remove the cooled dough from the refrigerator. Line a baking sheet with parchment paper or a Silpat (though I prefer parchment paper, because the dough will expand a bit less during baking).

Slice the dough logs into ½″ cookies. Lay flat on the prepared cookie sheets about 1″ apart.

Bake for 11–12 minutes. Let the cookies cool on the sheet for about 3 minutes before transferring to a wire rack to finish cooling. Man, these cookies are delicious, and so festive!

Chocolate Peppermint Pinwheels

adapted from Alton Brown
makes about 3½ dozen

Ingredients:
1 cup unsalted butter, softened
1 cup sugar
1 egg
1 egg yolk
1 tbsp. milk
3 cups flour
¾ tsp. baking powder
¼ tsp. salt
3 oz. unsweetened chocolate
1 tsp. vanilla extract
1 oz. white chocolate
½ cup crushed candy canes (about 6 canes)
confectioner’s sugar for rolling out dough

Directions:
Cream the butter and sugar in a mixer bowl. Add the egg, yolk, and milk and beat to combine. Scrape the sides of the bowl and beat again for 1 minute.
Meanwhile, whisk together the flour, baking powder, and salt. With the mixer speed on low, gradually blend the flour into the butter mixture.
In a medium bowl, melt the unsweetened chocolate. Stir in the vanilla, then incorporate half of the sugar cookie dough. Use a large spoon or hands to work the chocolate through until the color is completely even. Cover with plastic wrap and refrigerate for 5 minutes.
In another medium bowl, melt the white chocolate. Incorporate white chocolate and crushed candy canes into the remaining dough, stirring until the mint is evenly distributed. Cover with plastic wrap and refrigerate for 5 minutes.
Dust a work surface with confectioner’s sugar. On one side of the workspace, roll out the chocolate dough into a ¼″-thick rectangle, about 9″x14″.
On the other side of the workspace, roll out the white chocolate peppermint dough into an equal rectangle.
Carefully lift the peppermint dough onto the chocolate dough and press down to seal them together (ultimately it may be necessary to press the peppermint dough into a solid rectangle once on top of the chocolate dough, as it is very soft and likely to rip when lifted off the workspace). Cut the dough in half lengthwise (to create two very long, narrow rectangles). With a light touch (or with the help of wax paper or a Silpat underneath the layers), carefully roll up each rectangle into a long, skinny log. Wrap in wax paper and refrigerate for 2 hours.
When ready, heat the oven to 375°.
Cut the cookie logs into ½″ slices. Place flat on a baking stone or parchment paper–lined cookie sheet about 1″ apart.
Bake for 11–13 minutes. Let cool for 2 minutes before removing to wire racks.

Enjoy!