Chocolate Cookies… filled with Pumpkin Pie!


Repeat after me: Y-U-M.

pumpkin cookies

Now repeat a few more times.

Yum yum yum.

Yum yum.

Yum.

pumpkin cookies

These cookies are soft, rich, chocolatey… and filled with pumpkin pie!

Oh my.

If you own the cookbook, Vegan Cookies take over your Cookie Jar, you’ll probably remember one of the yummiest-looking cookies in the book: their peanut butter chocolate pillows. When I saw that particular recipe, I fell in love with the concept of a “stuffed” cookie. The possibilities swirled through my head like a soft-serve frozen yogurt machine.

Why stop at peanut butter?

I could stuff cookies with raspberry jam, with chocolate fudge, with pumpkin…

pumpkin cookies

Today, we’re going with pumpkin.

“Inside-Out” Chocolate Pumpkin Cookies

Filling inspired by Pumpkin Peanut Butter.

  • 3/4 cup white-ww flour (or white or spelt)
  • 6 tbsp plus 1 tsp cocoa powder
  • scant 1/4 tsp salt
  • 1/4 tsp baking soda
  • 1/4 cup plus 2 tbsp sugar (xylitol might work, but I haven’t tried it)
  • 2 tbsp maple syrup or agave
  • 3 tbsp milk of choice
  • 1/2 tsp pure vanilla extract
  • 3 tbsp plus 2 tsp vegetable oil
  • 3 tbsp pureed pumpkin
  • 3 tbsp nut butter of choice (I used pb. For a fat-free option, a few readers have subbed more pumpkin. I can’t personally vouch for it, though.)
  • 1/4 tsp cinnamon
  • 1/2 packet stevia (or 1/2 tablespoon sugar)
  • 1/8 tsp pure vanilla extract

Combine first 5 ingredients, and mix very well. Add ingredients 6-9 and mix again to form dough. In a separate bowl, combine all other ingredients to make the filling. Using about a heaping tablespoon of dough, roll into a ball and then flatten. Place a little scoop of the filling in the center and fold up the sides of the dough. Form into a ball. (The sides might crack a little, but that’s ok. They don’t need to be perfect.) Bake at 330 F (preheated) for around 10 minutes. They should be a little undercooked when you take them out. Let stand 10 minutes… if you can wait that long!

View Nutrition Information

 

chocolate pumpkin cookies

Fill in the blank:

What would be a dream cookie filling?

Mine would be filled with this recipe: Healthy Nutella.

I’m also dreaming up ways to do a mint filling.

Meet Katie

Chocolate Covered Katie is one of the top 25 food websites in America, and Katie has been featured on The Today Show, CNN, Fox, The Huffington Post, and ABC’s 5 O’clock News. Her favorite food is chocolate, and she believes in eating dessert every single day.

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223 Comments

  1. Ashley Pomes says:

    Great Recipe! I cannot wait to make this for thanksgiving next week. I was wondering if I could replace the oil with applesauce and if Bob’s Red Mill Gluten Free Flour would work. Thanks!

    1. eValerie says:

      Ashley — I made the cookies gluten-free (see my comment below for details of what I did). I think Bob’s Red Mill Gluten Free Flour should work, but I’d also add 3/8 teaspoon of either xanthan gum or guar gum, so that the cookies don’t fall apart. (If you use guar gum, you’ll also need to let them cool before handling, because guar gum doesn’t stick things together until they cool down after baking.)

  2. anonymous says:

    OMG these were soooooooooooooooooooo good!!! Everyone make these now!!!

  3. eValerie says:

    Oh My Goodness — these are the best cookies I have ever made!!!! And I have made a lot of excellent cookies in my life!!!!!

    We have lots of food allergies at my house, so I made the cookies gluten-free by replacing the flour with 1/4 cup brown rice flour, 1/4 cup garbanzo flour (if I wasn’t making them for my family, I’d have used quinoa flour instead of garbanzo, because some people hate the taste of garbanzo flour), 1/4 cup potato starch, and 3/8 teaspoon of guar gum. I also left out the salt, used sugar whenever there was a choice between sugar and another sweetener, used water instead of milk, and used almond butter instead of peanut butter — which was amazing!!! Oh, and I used freshly cooked pumpkin.

    Because of the nut butter and cinnamon, the pumpkin filling was fairly brown-colored, not the bright orange in the picture. I was disappointed by that and will use all pumpkin for the filling next time, and less cinnamon, to make the pumpkin color much brighter. I am thinking about replacing the cinnamon with pumpkin pie spices, because I think those would taste amazing in this recipe.

    My cookies flattened out a lot when they baked, into standard cookie shape with just a very thin layer of filling inside. That made them super moist and soft, and even more so after they had sat in the refrigerator overnight.

    The original recipe doesn’t say what the yield is, but I got 9 cookies, plus lots of very yummy extra filling left over, which I ate plain. Each cookie held about 1/2 to 3/4 teaspoon of filling.

    Katie, many thanks for this awesome recipe!!

    1. Chocolate-Covered Katie says:

      Thank you for trying them! 🙂

  4. Amber says:

    hi! i was wondering would GF all purpose mix work for this too?:)

    1. Chocolate-Covered Katie says:

      Sorry, I haven’t actually tested this recipe with a gf mix so I don’t know.

  5. Hannah says:

    I’ve got a container of pumpkin puree in the fridge with nothing to do but sit around and be agreeable. (Or mold, heaven forbid. 😉 ) Lets hope these cookies will happen soon, and that my trailer oven won’t destroy them.

  6. Carrie says:

    These are SO good. I just finished making them for my boyfriend who’s on the road and scheduled to be back tomorrow. He’s going to love them. I had to try one or two, just to make sure they were okay. DEFINITELY okay. Thank you so much for the recipe. Definitely a new favorite.

  7. Haley says:

    When you say “white-ww flour”, could I use one part white one part whole wheat flour? Or would that not have the same effect as using actual white-ww flour?

  8. Trajayjay says:

    Raw choco chip cookie dough
    Larabar
    Coconut shreds
    Caramel
    Melted chocolate
    Melted cheese

  9. Angela says:

    I made these with WW Flour, substituted 2 teaspoons of oil for applesauce and substituted 2 tablespoons of PB with Pumpkin. Turned out fabulous! Next time I’m going to drop a few chocolate chips into the pumpkin mix—just because you can never have too much chocolate!

  10. Sam says:

    Made these as printed — DELICIOUS!!! I had to add a teeny bit of water to the chocolate dough though. I have also honed my filling/pinching technique… thank you for an awesome recipe, these are so good.