Checkerboard Cookies

I’d be lying to you guys if I said I wasn’t kinda ready for the summer to end. In the first place, I don’t much care for extreme heat and as I’ve said in a couple of recent posts, the heat here has been unnecessarily extreme to the point where I’ve retreated to whole different cities for the day because this desert valley we’re in feels too much like a…desert valley. In the second place, the sooner the summer ends, the sooner we can get to the autumn which is my favorite season. The sooner autumn comes around, the sooner we can get to December and my favorite holiday of Christmas.

Because yes, my thoughts are definitely already drifting towards Christmas.

To be honest, I usually start getting the ‘itch’ for Christmas in July. It’s like a Christmas in July effect takes over and suddenly I’m listening to my holiday playlist again and planning what new stuff I’m gonna try to cook and bake for my family and the blog. As some of my followers know, I do a yearly Christmas series of recipes and although it’s a heavy undertaking, it is one that I still look forward to doing. I’ve already got a few pegged in my mind for the series, but one of them in particular was one that I thought would be a good idea to practice with first, as it is one I’ve never done before and would require a little bit more effort.

When I was little, I loved checkerboard cookies. I thought they just had to be some kind of food wizardry that could only be done in a huge Keebler-Elf style factory with a fancy machine.How else could they arrange those two different colors/flavors in such perfect patterns? I also may as well as admit that until only recently I had no idea how it was done or that it COULD be done by a home cook/baker in their own kitchen.

But I learned. And then after studying the technique a bit, thought “Well, might as well try it out. What’s the worst that can happen?”

(Waste of dough and ingredients was the answer, but that’s kind of obvious.)

I knew going into it that it wouldn’t be necessarily easy and I will keep it one hundred with you guys: I wouldn’t recommend trying this recipe if you don’t genuinely like to bake, have some experience with working with cookie dough and are willing to be patient with yourself and the process. I’m a decent baker with quite a bit of experience working with cookie dough, I love doing it and (as you can see) my first try at checkerboard cookies still wasn’t exactly perfect.  Nevertheless, I’m still pleased with how these turned out and that I decided to do a test run before trying to make a ‘Christmas-themed’ version for the 12 Days of Christmas series.

I tried to make the directions for these as clear and detailed as possible. So, should you want to make these for yourself (and I do think you should), a few pointers: a ruler is a must here. You’re making two different cookies doughs and when you cut them, you want the portions to be as straight as possible so that when you arrange the strips, they actually look like squares. It doesn’t have to be fancy invested in a regular old blue plastic ruler that measures inches/centimeters that I bought from Target and use strictly for baking; it does the job just fine. Also, when you’re putting the doughs together to create the pattern, don’t beat yourself up if your squares don’t line up perfectly in a row. Mine don’t and I still think the integrity of the ‘checkerboard’ is preserved in the overall aesthetic of the cookie. I plan to get better the more I practice this and I’m sure you will too.

You don’t have to make the two outer ‘wrappings’ for the cookies. I just thought it looked prettier so I decided to go ahead and make some. All you’ll need to do after making the cookie recipe is halve the base recipe and use the two different doughs from the halved recipe to wrap the cookies. It sounds complicated, but it’s not. Just read the recipe closely ahead of time and you’ll do fine.

Finally, don’t you dare throw out those scraps after you trim your dough logs! Cut them into mini pieces like I did and bake them off so that you get ‘bite sized checkerboards’ like the ones you see in the picture above. Aren’t they just as cute?

The labor alone involved in making these cookies make the finished product worth it–but I gotta say, the taste wasn’t a letdown either. Checkerboards have a close texture that’s slightly crisp on the outside, then buttery melt-in-the-mouth tender on the inside. The real dilemma here is going to be deciding which flavor you like better: the one where the vanilla dough is dominant or the one where the chocolate one is. I think I’m partial to vanilla, but that could very well change by Christmas time. We’ll have to see.

Linking this post up to Fiesta Friday #186, co-hosted this week by Colleen @ Faith, Hope, Love & Luck and Alex @ Turks Who Eat.

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Checkerboard Cookies

Recipe Adapted from “Classic German Baking” by Luisa Weiss

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Ingredients

  • 20 plus 1 tablespoons (300g) unsalted butter, softened to room temp
  • 18 tablespoons (150g) powdered sugar
  • 1/4 teaspoon salt
  • 1/2 teaspoon vanilla extract
  • 3 1/3 cups, minus 2 tablespoons (400g) all purpose flour
  • 5 tablespoons cocoa powder
  • 1 egg yolk
  • 2 tablespoons milk

Directions

In the bowl of a standing mixer or a large bowl using a handheld mixer, beat butter until it is light and creamy. Add the powdered sugar and salt and continue to beat about 1 minute more until creamy again. Add the vanilla extract and beat until just combined. Add the flour in 1/2 cup increments, until just combined. (Use a rubber spatula throughout mixing, scraping down the sides of the bowl to ensure even mixing)
Scrape out half of the dough, form into a flat disk and wrap in plastic wrap. Add the cocoa powder to the remaining dough in the bowl and mix until combined. Form the dough into another flat disk and wrap in plastic wrap. Place both in the refrigerator for at least one hour.

Remove dough from the fridge. Unwrap one of the discs, then place in between two sheets of wax paper or plastic wrap. Use a rolling pin to roll out into a rectangle, about 8 x 5 inches long. Repeat with the second dough. In a small bowl, beat together the egg yolk and milk. Using a pastry brush, brush the egg wash over the bottom rectangle of dough. Place one rectangle on top of the other. Press to adhere them to each other. Trim the edges with a sharp knife and save the striped strips in the fridge. Divide the rectangle lengthwise in half. Refrigerate the halves for about 15-30 minutes to allow to get firm.
Divide each of the halves into fourths, lengthwise. (A ruler or bench scraper works GREAT for ensuring straight lines) Use the four layers to make TWO checkerboard logs: Brush the tops of two of the layers with the egg wash, then place the other two on top of them. Make sure that you flip the top layers upside down before adhering so as to create the checkerboard pattern. Use your fingers or a spatula to press the logs together and smooth out the edges/corners, try to make them as square as possible. Wrap the logs in plastic wrap and refrigerate for at least one hour.

Preheat oven to 350°.

(If you would like to create the ‘outer wrapping’ for the cookies: halve the original cookie recipe and follow the same instructions, dividing the two colors, wrapping them in plastic wrap and placing in the refrigerator. After you’ve finished creating the two checkerboard logs, roll one of the reserved dough discs out between two pieces of plastic wrap or wax paper into a long rectangle. Place one of the chilled logs on the rectangle, on the edge closest to you. Wrap the dough around the log, press lightly on the bottom to seal and trim any excess. Repeat with the other color and log. Refrigerate both for about another 30 minutes to allow to firm up.)

Use a sharp knife or bench scraper to cut the log cross-wise into slices. Place sliced cookies on prepared baking sheets lined with parchment paper or aluminum foil. Bake in the preheated oven on the middle rack for 12-15 minutes, until just light golden brown. Allow to sit on baking sheet for about 60 seconds removing to wire racks to cool completely. Cut the reserved trimmings into bite sized nuggets and bake for about 13 minutes. Remove to a wire rack to cool completely.

(No one oven is the same, & different baking sheets bake cookies differently. Keeping this in mind, I will ALWAYS test bake one cookie before baking entire sheets of the whole batch, just to get a good idea of how long they should be in the oven and if I need to adjust the way I’ve cut, rolled them out, etc. I highly recommend that you do the same.)

21 thoughts on “Checkerboard Cookies

  1. It is my dream to make cookies like these, but I am just so lazy!😩 These look so pretty and I am sure these taste awesome, too! Thanks for sharing, Jess! Happy Fiesta Friday!

    • Haha, you know for a long time that was what was keeping me from making them too Jhuls. But once you just do it, it’s so rewarding when they come out at least mostly like you want them to. Thanks, I hope you’ve have a good weekend 🙂

  2. Haha I love the vision of a magic Keebler elf making these. I’m glad that you could master the magic yourself! These look absolutely perfect, great job!

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