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Chocolate Cookies… filled with Pumpkin Pie!

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Repeat after me: Y-U-M.

pumpkin cookies

Now repeat a few more times.

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!

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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.

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Katie is the baker, photographer, and author of the popular blog Chocolate-Covered Katie. Her favorite food is chocolate, and she believes in eating a balanced diet that includes dessert every single day. More about Katie—> 
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  1. These look delish! My dream cookie would be filled with peanut butter AND cookie dough! Is that possible?? 🙂

    1. Andrea says:

      Peanut butter cookie dough!

  2. My dream cookie would be filled with…melted chocolate? peanut butter? raspberry jam? cannot choose!

  3. KATIE YOU ARE SUCH A GENIUS!! These look AMAZING and I will definitely be making them ASAP!! My dream ones would be filled with melted chocolate and PB mmm… 🙂

  4. Hannah says:

    These look delicious!
    My dream cookie would be filled with…well, why go through the dilemma of choosing between peanut butter and cookie dough? Why not peanut butter cookie dough! 😀

  5. I’m gonna try this! I just pureed an entire pumpkin today! My dream cookie would be filled with COOKIE DOUGH!!! 😀

  6. Renata says:


    These look heavenly… I think I would love a HAZELNUT CREAM stuffed chocolate cookie… mmmmm

  7. Mine would be full of…more chocolate!

  8. Oh my! These look delicious! YUM!

  9. Ashley says:

    Like the first person said, peanut butter and cookie dough does sound amazing. What about peanut butter and white chocolate?

  10. Susan says:

    I’m having a housewarming party tonight and I am going to make these. THANK YOU!!!!!!!!!!!!!!

  11. Jennifer JCD says:

    Mmmm…. pumpkin stuffed cookies!! Yum yum yum!!

    My favourite filling… hmm… I’m not sure if I can think of anything better than pumpkin. Fruit would be nice, but I think pumpkin is still better!

  12. You are SOO amazingly creative! I never would have thought of this, but it sounds wonderful. Your photos are soo attractive too. Keep up the good work – love these healthier options!

  13. I’m picturing a red velvet plump cookie filled with white cream cheese frosting. That would be visually so appealing but more importantly sooo delicious!

  14. Crafty lil vegan says:

    Oh my! These sound devine! he perfect filled cookie? – Chocolate S’more!!

  15. my ideal cookie would be filled with….Mint ice cream…but dang girl!! These look and sound fantastic 🙂

  16. Ambika S. says:

    I wonder if this would work with a soft gingerbread cookie on the outside, same filling on the inside… !! that would be amazing for thanksgiving!

    That. Looks. Awesome!

  18. Wow! These look awesome! I’ve seen so many delicious baking recipes this week, I don’t know which to try first, but these are definitely a contender! My dream cookie would be filled with… Nutella!

  19. Megan says:

    I have the biggest smile on my face right now! I looked at the time…almost 10:00…time to check CCK. As soon as I saw the title of the post, CHOCOLATE HEAVEN. These cookies look so amazing I want one right now! Thank you Katie!!!! My dream cookie? Well, you’ve made one already and Isa has too, so maybe a dark chocolate filled cherry cookie? Or a dark chocolate with a creamy hazelnut mocha filling?

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