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.

You may also like

Don’t Miss Out On The NEW Free Healthy Recipes
Sign up below to receive exclusive & always free healthy recipes right in your inbox:

Leave a comment

Your email address will not be published. Required fields are marked *

223 Comments

  1. Sarah says:

    I love your recipes and have made several – lots of delicious things! This was one of my favorites. I used a mix of oat flour and coconut flour, and for the sweetener did an equal mix of erythritol, xylitol and coconut sugar with a dash of stevia. I also used butter for most of the oil and they turned out wonderful. I guess I scooped the chocolate far too thick though because I only got about 12 out of it and had quite a bit of leftover pumpkin-almond butter mix (which is delicious and will get used obviously, elsewhere). Thanks for all of your great posts – very inspiring and enjoyable to read.

  2. Patricia says:

    Hi Katie,

    I think that what you are doing is great, trying to make everyones favorite guilty treat healthy; but as a future Dietetics student I have to ask!

    Where do you get your nutrition info from? Are you a registered Dietitian or Nutritionist? How can we the people trying these recipes know that your nutritional estimations are accurate?
    A REPLY would be greatly appreciated!

  3. Sarah says:

    I made these for a Harry Potter party and called them chocolate pumpkin pasties. They are AMAZING. I’m kind of fearful though cause I was only able to make 11 cookies so I think I managed to eat half the dough O.O they are so great.

  4. Shandra Grace says:

    Katie! I loved this recipe so much! I am doing online school this year, and one of my courses is Foods (Grade 10) I had to make a cookie recipe, and I chose this one, these were the best cookies I’ve ever had, and people love them!! One thing I am confused about is that the cookies were extremely moist, I could hardly wrap the dough around the filling because it was so soft, I know I followed the recipe exactly. I used olive oil, so maybe that had something to do with it.

    Thanks so much for sharing this amazing recipe, it is to die for!! 🙂

    Shandra <3

  5. Kelly S. says:

    I made these tonight and they are YUMMY. Mine don’t taste very pumpkin-y- I just taste PB- but that isn’t really a bad thing. They still taste good! 🙂 I got 17 cookies out of the recipe.

    I found it easiest to make them assembly-line style: I smushed out a bunch of dough rounds and laid them out, then dropped filling on them all, then kind of rolled up the dough to cover the filling. They turned out prettier when I did them this way!

  6. Ashley says:

    Just pinned these! Fingers crossed for the Food processor! 😉
    I have frozen these and they taste really good right out of the freezer! (I tried to freeze them to save them for another occasion, but they last just a few days when I kept sneaking them out one by one!) 🙂
    Thank you for all the wonderful healthy recipes!

  7. Anonymous says:

    holy awesome!!!

  8. Cathy says:

    Making these for Thanksgiving! Always looking for new things to try for the gathering. They look awesome!

  9. Meg says:

    I read your website daily and have loved every recipe of your I have tried! I’m a big pumpkin fan and am excited to try this one out! I made one of each of your single-serving cupcakes for my hubby last weekend and he loved all of them, especially your pumpkin chocolate chip cupcake!

  10. Eco Chic says:

    Just made these! I used pb and applesauce in place of the oil and I think they tasted good but I don’t know how they are in comparison to the original. There is one cookie left and I live with omnivores… Made them only a few hours ago. I love pumpkin in the fall!! My dream cookie filling would have to be more chocolate. Like melted chocolate in a ball of cookie dough. Yum!!! I love all of your recipes I have tried! My favorites are your ice creams and cookies! The simpler, the better 🙂

  11. Elle says:

    Katie, I made these this afternoon…and for some reason they taste so awful. Problem#1, Instead of 1/4 cup o sugar and 2 TBS, I used stevia instead. My conversion chart said that baking stevia was the same measurements as sugar. problem #2, too much SALT. I used just as much directed, and for some reason, they are SO salty. Problem #3, after doing as instructed for the dough, I found it to be VERY dry and crumbly. It was hard to form the dough because of the crumbly texture, and it had white specks all throughout. To help this, I added oil. Even after adding about 1-2 TBS more, they came out of the oven dry and gross 🙁 Please help me resolve my super-salty/stevia-ie cookies :/

    1. Chocolate-Covered Katie says:

      Unfortunately, I can’t recommend making a big substitution like you did (the stevia). I can only vouch for the recipe if you make it as written, as that’s the only way I’ve tried, and altering the ingredients will alter the result.

  12. flowerek says:

    It´s a great recipe. I had to give a little bit more flour to the chocolate dough so that it isn´t so sticky, but they were perfectly yummy! I made them with peanut butter and xylitol instead of sugar.

  13. 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.)

  14. anonymous says:

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

  15. 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! 🙂

  16. 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.