Fill-in-the-Blanks Pinwheel Cookies

Fill-in-the-Blanks Pinwheel Cookies
From left to right: Cranberry Pinwheels, Raspberry Pinwheels, and Nutella Pinwheels

Friends, I have found Parental Cookie Nirvana: Meet the Fill-in-the-Blanks Pinwheel Cookie. One recipe, made in stages (so it’s a Nap-Friendly Recipe), and so flexible that you can flavor it with just about anything that’s spread- or sprinkle-able. Oh, and once they’re rolled up and well-wrapped the dough can stay in the freezer for months, just waiting for you to slice off a few cookies and bake them up.

These Pinwheel Cookies were inspired by an abundance of Slow Cooker Maple-Apple Cranberry Sauce, but once I got going I wound up making four different varieties. In addition to the cranberry pinwheels, which baked up the largest (and the softest), I made batches with warmed Nutella and raspberry jam (the latter got tossed in cinnamon sugar, for a rugelach-y effect) and finely chopped bittersweet chocolate.

Those chocolate pinwheels were my favorite, but I didn’t get a picture—they weren’t the most attractive cookies in the world. I chopped the chocolate a little too large and the dough burst while rolling. They were the ugliest, most addictive little cookies I’ve had the pleasure of popping into my mouth, one after another.

Together with a batch of Samoa Cookie Bars, I’ll be bringing some of these to tomorrow’s NYC Cookie Swap fundraiser. Can’t wait to see what I’ll come home with!

Pinwheel Cookies
Makes 6-8 dozen

Pinwheel cookies are fairly common, but my version uses almond flour, which gives the dough a nice warm flavor (not to mention a nutritional boost). If you don’t have it, just use 100% all-purpose flour.

2 cups flour, plus more for rolling
2 cups almond flour
1/2 teaspoon salt
1 cup butter (2 sticks), softened
1 1/2 cups sugar
2 eggs
2 teaspoons vanilla extract
1-2 cups filling of your choice: jam, leftover cranberry sauce, Nutella, very finely chopped chocolate
1/4 cup demerara sugar with 1 teaspoon cinnamon, optional

  1. Combine the flours and salt in a medium bowl and set aside.
  2. In a stand mixer fitted with the paddle attachment or a large bowl with an electric mixer, cream together the butter and sugar. Add the eggs and vanilla, and mix until combined. With the mixer on low, gradually add the dry ingredients, mixing until just incorporated.
  3. Lay out four large pieces of plastic wrap, and divide the dough equally onto them. Use the wrap to shape each one into a squarish shape, then wrap tightly and refrigerate for at least an hour.
  4. If your filling needs warming to make it spreadable, warm about 1/4 cup now (15 seconds in the microwave is usually enough for mine). Lightly flour a piece of parchment or Roulpat, and roll one of the dough squares into a rectangle approximately 9 x 12 inches. Don’t roll it too thin or the dough will be too delicate for what follows. Gently spread the filling over the dough, leaving about an inch exposed on one long side. You may not need all the filling—if it’s spread too thick it’ll ooze out while baking.
  5. Starting from the filling-covered long side, carefully roll up the dough, jelly roll-style. Cut it in half crosswise if it’s unwieldy, wrap tightly with plastic wrap and then foil, and freeze. (If you’re making more than one variety, be sure to label the logs!) Repeat with the remaining squares of dough and filling.
  6. When they’re frozen solid—wait at least 6 hours, preferably overnight, and up to three months—preheat the oven to 375°F and line two baking sheets.
  7. Use a serrated knife to slice the logs roughly 1/3” thick. If you’re using a jammy filling, press both sides of each cookie gently into the cinnamon sugar. Place about an inch apart on the baking sheet. They don’t spread much, so I was able to fit 16 on each sheet.
  8. Bake for 12-15 minutes, rotating placement of the sheets halfway through, until cookies are lightly browned. Slide the Silpat or parchment with the cookies to a rack, and when cookies are set (2-3 minutes) transfer to the rack to cool fully.

MAKE BABY FOOD: Nope, sorry. They’re technically safe (though if there are nut allergies in your family, check with your pediatrician) but filled with sugar.