Chocolate-Topped Pumpkin Pinwheel Cookies

Chocolate-Topped Pumpkin Pinwheel Cookies

Stack of pumpkin pin wheel cookies

Are you a Morning Person? I’ve become one. I think we can be irritating to others, we Morning People. Chatty, renewed, refreshed. Excited! Annoying.

I used to be a Nothing Person. I was never a night owl like my husband, and never really seemed like much of a morning person either. What did that make me? Sad. It made me sad. I used to know someone who insisted that she was not an afternoon person. She was no good in the afternoons, she said. What the heck does that mean anyway? I don’t even much like that person, who used to insist that, so I can’t even ask her. I just have to go on wondering. Anyway, she used to work for me, and I think she was just trying to get out of having too much asked of her in any given day.

I wish I were the type of person who could live with telling someone I worked for, Hey, I would totally do that project for you, except it’s going to require some afternoon work, and I’m just really not an Afternoon Person. Like that’s a thing.

It’s not a thing. Is it?

Rolled up cookie doughPerson going to grab a pumpkin pinwheel cookie

Know what’s absolutely a thing? Pumpkin pinwheel cookies, half-dipped in chocolate. Well, it’s at least A Thing now. Here’s how these lightly sweet, soft, pretty little things came about.

Stack of pumpkin pinwheel cookies

I was all set to add some orange food coloring to the vanilla layer of these Gluten-Free Pinwheel Cookies, and serve them as a Halloween treat. They’re really light and buttery, and I so enjoy them and their vanilla-chocolate charms. Then I got scared of the no-food-coloring-people again. They’re like body-snatchers, those people. That’s when I realized something (probably in the Morning).

Pumpkin is orange. That’s even the wholereason we have orange things on Halloween. That’s how it went. Exactly like that.

These pinwheel cookies are lightly sweet and fragrant with pumpkin pie spice, perfect for the season. Where the traditional chocolate-and-vanilla GF pinwheel cookies are crumbly and melt-in-your-mouth-buttery, these cookies are thick and soft. And the rich hard chocolate tops (or bottoms, depending) are the perfect complement to the chewy soft cookies below (or above, depending). And, not for nothing, but the spirals make a rather impressive presentation. Don’t you think?

Like this recipe?

Prep time: Cook time: Yield: 20 cookies


2 1/2 cups (350 g) high-quality all-purpose gluten-free flour

1 teaspoon xanthan gum (omit if your blend already contains it)

1/2 teaspoon baking powder

Dash (1/8 teaspoon) baking soda

1/2 teaspoon kosher salt

3/4 cup (150 g) sugar

8 tablespoons (112 g) unsalted butter, at room temperature

1 extra-large egg at room temperature, beaten

3/4 teaspoon pure vanilla extract

5 ounces pure packed pumpkin

2 1/2 teaspoons pumpkin pie spice

2 tablespoons (16 g) cornstarch

1/4 cup (2 fl. oz.) cream, at room temperature

12 ounces semi-sweet chocolate, chopped


  • Preheat your oven to 375°F. Line a rimmed baking sheet with unbleached parchment paper and set it aside.

  • In a large bowl, place the flour, xanthan gum, baking powder, baking soda, salt and sugar, and whisk to combine well. Add the butter, egg and vanilla, mixing well after each addition until the dough comes together. It will be thick, and a bit crumbly. Divide the dough into two portions, one about 10 ounces, one about 16 ounces, and set the larger portion aside.

  • Place the smaller portion of  dough into a medium-sized bowl, and add the pumpkin, pumpkin pie spice and cornstarch, and mix to combine. Place the pumpkin dough in between two sheets of parchment paper, and roll into a rectangle about 1/4 inch thick.

  • Place the larger portion of dough into a medium-sized bowl, add the cream, and mix to combine. Roll out plain vanilla dough in the same manner as the pumpkin dough. Place both pieces of rolled out dough on a large baking sheet, and place in the freezer for about 15 minutes, or until firm (but not rock solid, or it will begin to crack).

  • Once the dough has chilled, remove all but one piece of parchment paper from both pieces of dough. Place the one side still lined with parchment paper on the kitchen counter, parchment side down. Place the other piece of dough squarely on top of the first. Starting at a short end of the rectangle and using the bottom sheet of parchment paper to handle the dough, roll the dough away from you and into a cylinder that is as tight as you can manage. Remove the parchment paper, and wrap the roll tightly in plastic wrap.

  • If there seems to be a gap in the very center of the cylinder, roll the dough back and forth on the counter, from the center out, to fuse the center. Chill the roll of dough in the freezer for about 10 minutes, or until firm.

  • Remove from the freezer, slice in 1/4 inch cross-section. Place less than 1 inch apart on the prepared baking sheet, and bake for about 12 minutes, or until the cookies are set and just beginning to brown a bit. Allow to cool completely on the baking sheet.

  • While the cookies are cooling, melt the chocolate. In a small microwave safe bowl, place the chopped chocolate. Microwave on 70% power for 40 seconds. Stir. Microwave for another 30 seconds and stir again. Repeat in 30 second intervals until the chocolate is melted and smooth. Allow to cool slightly.

  • Once the cookies are cool, holding each cookie by the edge, dip it halfway into the melted chocolate and bob it up and down a few times. Carefully invert the cookie and place it, chocolate side up, on a clean piece of parchment paper. Allow to cool at room temperature until the chocolate is set.


P.S. If you haven’t yet, please pick up a copy of My Cookbooks! I can’t keep the blog going without your support!

Where should I send your free guide?

By entering your email, you're agreeing to our Privacy Policy. We respect your email privacy, and will never share your information.