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!

Comments are closed.

  • MeridithE
    October 18, 2012 at 5:57 PM

    Can the rolled up dough be chilled overnight to be baked the next day?  Can it be frozen?  

    • Notime911
      October 20, 2012 at 8:45 PM

      would like to know the answer to that one also.  

    • gfshoestring
      October 21, 2012 at 10:34 AM

      Hi, Meridith,
      It can definitely be chilled overnight and then baked the next day (I would chill it unsliced), but I haven’t tried freezing it. You’ll have to experiment!

  • October 17, 2012 at 12:30 PM

    Nicole, we made these last night…..wonderful recipe!  Even my son who is afraid of pumpkin anything except carved pumpkins couldn’t wait to try them because they were so fun looking!  Thanks for such a neat recipe! 

    • gfshoestring
      October 17, 2012 at 4:22 PM

      It’s a good time of year for your son to get on the pumpkin bandwagon, Jennifer! Glad they were a hit.
      xoxo Nicole

  • Alison
    October 16, 2012 at 9:03 PM

    Sorry for the totally off topic question…I’m planning on baking your White Sandwich Bread (cookbook pg. 104) tomorrow, but have one question…I made up your mock Better Batter to use for the bread.  Since the mock BB has xanthan gum in it already, do I still need to add the extra amount in the recipe?

    Thanks!  So looking forward to the bread…really want bread that tastes and feels like bread!

    • gfshoestring
      October 17, 2012 at 8:26 AM

      No problem, Alison. Nope – omit the xanthan gum as an ingredient in the recipe since it is already in your blend!
      xoxo Nicole

      • Alison
        October 18, 2012 at 10:47 PM

        It is fantastic!  I think that I may not have let it rise for long enough…it didn’t look as fluffy as yours, but the taste and texture is still better than any other GF bread I’ve ever had!  :) and, I can’t believe it’s still fresh enough to eat without being toasted. 
        Any tips on getting the lovely loaf shape?  My loaf ended up being rather reactangular.
        Thanks, again!

        • gfshoestring
          October 21, 2012 at 10:34 AM

          Alison, you’ll need a higher rise. I’d work on that. Read the intro to the chapter on breads in the book for tips on that.

  • Mrs. GF
    October 15, 2012 at 9:36 PM

    Oh these are lovely! I think I will surprise my family with them tonight. Hubby is definitely a night owl so he will appreciate it. :-) As for me, I am a morning person….and annoying in my perkiness according to our teen daughter. LOL!

  • October 15, 2012 at 7:27 PM

    I sure wish I was a morning person especially since my kids get me at the crack of dawn (though an immediate cup of coffee helps!), but what I definitely am is a pumpkin (loving) person, a cookie person and a chocolate person, so thanks for this beautiful and fun and delish looking treat!

  • Hannah Washburn
    October 15, 2012 at 6:47 PM

    So I’ve been looking over your recipes and they look great! The only issue is that I’m doing dairy-free as well as gluten-free. I’ve seen a lot of recipes that call for sour cream … would it work if I substitute non-dairy yogurt?

    • gfshoestring
      October 21, 2012 at 10:35 AM

      I haven’t tried this recipe with any substitutions. Feel free to experiment!

  • Lhasapets
    October 15, 2012 at 1:56 PM

    Hi  Nicole
    I’ve  been  seeing  many  recipes  now  that  call  for  one  extra  large  egg. I usually only have  large  eggs  on hand, any  suggestions  or  would  just  a  large  egg  work?

    • gfshoestring
      October 15, 2012 at 5:01 PM

      Large eggs weigh 2.00 ounces, and extra-large 2.25 ounces. Feel free to experiment.

    • Lindsay Balez
      October 23, 2012 at 12:57 PM

      When I have made her recipes with large eggs, the recipes still work. Would they be somehow better with extra large eggs? Maybe! I usually just use the biggest egg in the carton and move on with my life.

  • Marcy
    October 15, 2012 at 1:35 PM

    Can I use DF coffee creamer in place of the cream? Hope so, cause I’d love to make these for Thanksgiving.

    • gfshoestring
      October 15, 2012 at 5:02 PM

      Coffee creamer almost always has a lot of extra ingredients in it. It is not an appropriate baking substitute for cream. Feel to experiment with another type of milk.

  • RebeccaLB
    October 15, 2012 at 12:50 PM

    Mmm….. more pumpkin!  These are going into my “Favorite Recipe” file!  I have been reviewing all of your cookie recipes getting ready for the holidays.  I used to send everyone boxes of cookies for the winter holiday season and couldn’t do the last couple of years – now that my kitchen is completely gluten free I refused to contaminate it again.  But I am feeling brave this year and will send everyone GF goodies and just not tell them they are GF.  My grandkids have been my guinea pigs and they love everything!

    • gfshoestring
      October 21, 2012 at 10:36 AM

      Holiday cookies are specialty around here, Rebecca! No reason to contaminate your kitchen. :)
      xoxo Nicole

  • Mary Hall
    October 15, 2012 at 12:32 PM

    Oh, if only these were crunchy…my cookies must be crunchy, as I’m somehow unable to get past the internal process of “These are soft! Are they finished baking?  They must be under-baked.”  Still, the pumpkin spice and chocolate aspect sounds delicious.

  • GFMom
    October 15, 2012 at 12:24 PM

    What if we only have large eggs and salted butter.  Most of your recipes call for unsalted butter and extra large eggs, does it make a big difference?

  • Jennifer S.
    October 15, 2012 at 12:08 PM

    I am a morning person and sometimes I feel like I am NOT an afternoon person.  Which I think means, our energy is a little lower at that time.  So I try not to schedule mtgs and stuff in the afternoon and to make sure I get a work out in so I can boost my energy if I have to host one or do a big project.  Back in the day – you could have suggested that to her! LOL!! : )

    I really like the looks of these cookies – so while the kids are at G&G’s this week I’m making them along with my first attempts at GF breads.  If they don’t turn out.. I’ll have these cookies to nosh on!

    Can’t wait for my 2nd cookbook to arrive! 

  • October 15, 2012 at 9:19 AM

    It calls for cream to be added to the vanilla dough, but I am not seeing that in the ingredients list.  How much do we need?

    • gfshoestring
      October 15, 2012 at 9:20 AM

      It’s the second-to-last ingredient in the list, Tiffany.

  • October 15, 2012 at 9:14 AM

    Oooo you combined two of my favorite things, pumpkin and chocolate. Thank you! =)

    • gfshoestring
      October 15, 2012 at 9:21 AM

      You’re so very welcome, Heather!
      xoxo Nicole

  • Mrs Ducky
    October 15, 2012 at 8:54 AM

    You know, facing Monday morning today seems a little easier after looking at these cookies…. YUMMMM! I can’t wait to make some.

    • gfshoestring
      October 15, 2012 at 9:21 AM

      Not a morning person, Mrs. Ducky? Glad I could help. ;)
      xoxo Nicole

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