Chocolate Cinnamon Checkerboard

These intricate, beautiful cookies look like small checkerboards. Admittedly, they’re a bit of work—you’ll need to make two doughs, weave them into a checkerboard pattern, then cut them into rectangular cookies. But the results are worth the extra effort: a crunchy, light, spiced cookie that’s sure to be a hit at every party, potluck, or family gathering.

2 ounces unsweetened chocolate, chopped
1 2⁄3 cups all-purpose flour, plus additional for dusting
1⁄4 teaspoon baking powder
1⁄4 teaspoon salt
8 tablespoons (1 stick) cool, unsalted butter, cut into small pieces
6 tablespoons solid vegetable shortening (3 ounces)
1 cup plus 2 tablespoons confectioners’ sugar
4 large egg yolks, at room temperature
2 teaspoons vanilla extract
1⁄4 cup granulated sugar
2 tablespoons ground cinnamon

1. Place the chocolate in the top half of a double boiler set over a pot of simmering water, or in a medium bowl that fits tightly over a medium saucepan of simmering water. Stir until half the chocolate has melted, then remove the top half of the double boiler or the bowl from the heat and continue stirring until all the chocolate has melted. You can also melt the chocolate in the microwave oven by placing it in a medium bowl and microwaving it on high for 20 seconds, stirring well, then continuing to heat on high in 15-second increments, stirring after each heating; when
about two-thirds of the chocolate has melted, continue stirring outside the microwave oven until all has melted. Transfer the melted chocolate to a clean, dry bowl and set aside to cool for 5 minutes.
2. Whisk the flour, baking powder, and salt in a medium bowl until well combined; set aside.
3. Soften the butter and shortening in a large bowl, using an electric mixer at medium speed; add the confectioners’ sugar and continue beating (on low at first, then at medium speed) until light and fluffy, about 1 minute. Beat in one egg yolk at a time, making sure each is thoroughly incorporated before adding the next. Beat in the vanilla. Remove the beaters and stir in the prepared flour mixture with a wooden spoon or a rubber spatula just until moistened. Gather the dough together into a ball.
4. Divide the ball of dough in half. You need a very precise reading of half for this recipe, so we suggest using kitchen scales to get an accurate measurement. If you don’t have a kitchen scale, scoop out the dough in 1⁄4-cup increments, going back and forth between two clean bowls until you’re sure you have half in each bowl. Stir the melted, cooled chocolate into one of the halves of the dough. (You may find it works best to use your hands.) Wrap each half in plastic wrap, flatten into thick disks, and refrigerate until firm but not rock hard, about 1 hour but not more than 3 hours.
5. Position the rack in the center of the oven; preheat the oven to 375°F. Line a large baking sheet with parchment paper or a silicone baking mat; set aside. Combine the granulated sugar and cinnamon on a large plate; set aside as well.
6. Unwrap the two sections of dough (one vanilla and one chocolate) and place them each on a lightly floured, dry surface. Dust each section of dough with flour, then roll or press each into an 8-inch circle, about 1⁄2 inch thick. Place the chocolate circle on top of the vanilla one; press very lightly to adhere. (The stacked dough is about 1 inch thick and you don’t want to lose its height or shape by pressing too hard.) Use a ruler to help you trim the circles into a 6-inch square. Set the trimmings aside for another use—see below for one idea.
7. Cut the square in half, then separate the halves somewhat. Cut each half into 3 long, 1-inch-wide strips. Flip the center strip in each half, thereby reversing the chocolate/vanilla combination in the middle of each of the 3-strip sections. Square up the edges of each half with a ruler or a dough scraper (in case the halves have bulged out while being cut), then press down again very lightly. Do not flatten—the point is to make sure the cookie strips are adhering to each other.
8. Dip one of these 3-strip blocks into the prepared sugar and cinnamon mixture on the plate, coating the top, bottom, and long sides, not the checkerboard ends. Return it to your work surface and slice it off into cookies slightly less than 1⁄2 inch thick, cutting across the stripes, or at a 90-degree angle to the strips on the top of the block (thinner slices produce crunchier cookies; thicker ones, cakier cookies). The cookies sliced off the block will be rectangles of about 1 × 3 inches. Place the cookies, cut side down, on the prepared baking sheet, spacing them about 1 inch apart.
9. Bake for 15 minutes, reversing the sheet front to back halfway through the baking process. The cookies should be lightly browned but still springy to the touch. Cool for 2 minutes on the baking sheet, then transfer the cookies to a wire rack to cool completely. Cool the baking sheet for 5 minutes (or use a second baking sheet lined with parchment paper or a silicone baking mat), then continue slicing and baking the remainder of the cookies.

Recommended storage
3 days at room temperature
2 months in the freezer

Suggestions for the Trimmings:
Combine the reserved trimmings into one ball. Roll out this dough on a lightly floured surface, then cut out 3-inch round cookies or any shape cookies, using a similarly sized cutter for marbleized cookies. Bake on a cookie sheet lined with parchment paper or a silicone baking mat for about 15 minutes at 350°F.
Pinch off sections of dough and roll them into balls about the size of a walnut. Roll these small balls in a mixture of 2 teaspoons cinnamon and 2 tablespoons sugar similar to the one in the base recipe. Flatten slightly with a fork, making a cross-hatch pattern. Place on a baking sheet lined with parchment paper or a silicone baking mat. Bake at 375°F for about 15 minutes, or until set but still somewhat soft.

Rating: 4.0. From 1 vote.
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