I Tried Making Perfect Checkerboard Cookies(Here’s the Foolproof Trick)

Because I excel at timing, I decided long after most normal people had long wrapped up their holiday cookie baking last December to make the checkerboard cookies, Sara, who works with me behind the scenes, has been steadily requesting for about a decade.
I was skeptical at first. I pictured checkerboard cookies as a ridiculous amount of work for something that would look cute but probably not taste particularly special — with the dark squares merely chocolate-colored rather than chocolate-flavored.

I tried several approaches: first a sugar-cookie–style dough, but the pattern didn’t come out as sharp as I wanted. A classic powdered-sugar shortbread looked pretty but had a dull texture. I finally found what I wanted in an egg-yolk–enriched sable — it offered good flavor and a delicate snap — and left me an egg white I could use to roll the cookies in bright sanding sugars. Using a higher cocoa percentage in the chocolate half produced satisfying chocolate flavor. I relied on my favored cookie techniques from my Unfussy Sugar Cookies: start with cold butter, roll the dough right away (no floured counter), then firm it quickly in the freezer. A few short freezes, some stacking and slicing, and you’ll have the sweetest checkerboards you’ll taste — with zero sweat.

I was surprised, then hooked — I couldn’t stop. I also used the same doughs for spirals and marbled cookies. While the checkerboards are the stars, I include directions for all three shapes below in case you’re tempted to drop everything and commit to these dazzlers.

Checkerboard Cookies

Servings: 30 to 36 cookies Time: 1 hour 15 minutes Source: Smitten Kitchen

If you’re using a stand mixer or food processor, you can begin with cold butter, cut into cubes. If you’re using a handmixer, room temperature/slightly softened butter is best.

At-a-glance

Make dough in a food processor:

Combine the granulated sugar, powdered sugar, salt, and 1 1/2 cups (195 g) of the flour in the processor bowl. Add cold, diced butter and pulse until it disappears into the mixture; continue processing until the mixture just begins to clump. Add the egg yolk (reserve the white) and vanilla, pulse to combine, and keep running the machine until one large — or a few smooth smaller — masses form.

Make dough in a stand mixer or with a hand mixer:

Combine butter, both sugars, and salt in the mixer bowl and beat until creamy. If you started with cold butter in a stand mixer, this will take a couple of minutes and you’ll need to scrape down the bowl a few times. Once combined, add the egg yolk (reserve the white) and vanilla; beat until incorporated. Add 1 1/2 cups (195 g) of flour and mix until it disappears into a smooth dough.

Both methods:

Divide the dough in half (each half will weigh about 270–275 g). Leave one half in the bowl or processor. Add the remaining 1/4 cup (35 g) flour to that half and mix just until combined; scrape it out — this is the vanilla dough. Add the second half of the dough back into the bowl and mix in the cocoa powder until even — this becomes the chocolate dough.

Heat oven to 350°F (176°C).

To checkerboard the doughs:

Place each dough half between two sheets of parchment and roll each into approximately 4–5 × 10-inch (10–13 × 25 cm) rectangles about 1/4-inch (6 mm) thick. Transfer both slabs to a cutting board or tray and freeze 10–15 minutes, until firm like cold butter but not rock hard.
Remove the top parchment from each slab (you can save them to line your baking sheet), stack the chocolate and vanilla layers, and press them together lightly. Cut the stacked slab in half lengthwise (forming two ~2 × 10-inch rectangles) and stack the halves to make one long, striped slab. Press gently to adhere and return to the freezer for another 10–15 minutes, until very firm but not completely frozen.
Remove the long slab and, with a very sharp knife and steady hand, cut lengthwise into eight 1/4-inch-wide slices. Arrange the first four slices into a checkerboard log, flipping two so the opposite color is on top. Do the same with the second group of four to form a second checkerboard log. Wrap each log in parchment and press them into long, squared-off logs to bind the layers. Freeze one last time for about 10 minutes, until solid to the touch.

To finish cookies:

Line a large baking sheet with parchment (you can reuse the discarded parchment from earlier). Beat the reserved egg white until loosened. Have your sanding sugars ready.
Unwrap the first checkerboard log. Brush it lightly with egg white and roll or sprinkle it with sanding sugar. (Most people use one color per log; the author cut each log into quarters and used a different color for each quarter.) Slice the sugared log into 1/4-inch-thick cookies and space them about 1 inch apart on the baking sheet (they spread slightly). Repeat with the second log to make more cookies.
Bake for 10–12 minutes, or until the undersides are golden brown. Let cookies rest on the sheet for 5 minutes to firm up, then transfer to a rack to finish cooling and crisping.

Do ahead:

Baked, cooled cookies keep for up to 3 weeks in a tin at room temperature.

spiral cookies

To spiral the doughs:

Roll both chocolate and vanilla slabs to 1/8-inch thick and stack, patting lightly. Chill 5–10 minutes until cold but not hard. Cut into two equal-width long pieces. With the vanilla as the outer layer, roll each half into a tight spiral (the author notes she forgot once and did the reverse, but vanilla outside usually looks better). Wrap each spiral in parchment, press into a firm log, and chill in the freezer for 15 minutes, until solid but not frozen. Then continue from the “To finish cookies:” steps above.

marbled cookies

To marble the doughs:

Roll both slabs to 1/8-inch thick and stack them. Cut into two stacked sections and squeeze each into a rough log; fold and mash each once or twice, then press the kneaded mounds together and reshape into long logs. Wrap tightly in parchment, pressing into firm logs, chill for 15 minutes until solid to the touch but not frozen, then proceed from the “To finish cookies:” instructions.

Note: I am always inspired by Susan Spungen’s expert cookie styling, and was here too in both the colorful edges she uses in these Zebra Stripes and the marbling technique she uses in her Marbled Tahini Shortbread.

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