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. Mary says:

    I’ve been searching all week for the perfect recipe for a fall party tonight! Perfect timing! Thanks! 🙂

  2. Albizia says:

    If it is a chocolate cookie, my dream filling would probably be coffee-flavored. If I can choose the cookie too, then it must be a dark chocolate-filled coconut cookie. Yum! But now I am hit by a pumpkin craving 😀 .

  3. Emily says:

    My dream cookie would be filled with peanut butter of cookie dough. Mmmmm. Now you’re making me hungry. I might have to make those.

  4. Chloe@LightOnMyFeet says:

    My dream cookie would be filled with cheesecake… almond butter cheesecake… Cookies n cream cheesecake… Or maybe even cinnamon cheesecake? Who knows all I know is now I’m craving cookies and cheesecake.

  5. Kristin @ STUFT Mama says:

    How about a mix of peanut butter and cookie dough. 🙂 You are too much. I wish my baking looked as good as yours! These are awesome!

  6. extreme banana bread says:

    Oh. my. goodness. I just made these with my mom for a potluck dinner tomorrow. Mind you when I said “boy do I have a recipe for you” and continued with “and its healthy too” my mom gave me the stink eye..until I let her try the filling…I think this recipe may have won her over to the healthy baking side..Thank you soooooo much for posting this recipe…soooo YUMMY 🙂

    1. Chocolate-Covered Katie says:

      Aww wow, I am so excited you made them already!

  7. Holly says:

    I totally made these today! I used Bob’s Red Mill GF Flour and I used 2TB cashew butter and 1TB peanut butter in the filling. And honestly, I’m not too crazy about them. Believe me, we’ll eat them, but just not what I had expected. My pumpkin filling looks nothing like yours, it looks like pumpkin mixed with peanut butter (which is NOT a bad thing, just not quite what I expected!) The cookie part is GREAT! I think I may use the “cookie” part of the recipe and try my hand at GF Cookies n’ Creme Ice Cream sometime!

    1. Sarah M says:

      I also had this problem! I kept checking the recipe to make sure it said Tablespoons, and not teaspoons for the nut butter. I ended up adding about 2 1/2 extra tablespoons of pumpkin to the filling mixture, and it was much better. I probably could have added even more! It worked out great making that one change…plus a little pumpkin pie spice for the depth of the cloves and the bite of the nutmeg 🙂

  8. Kelsey @ Snacking Squirrel says:

    i don’t think you could get a filling more perfect than this. They remind me so much of Tim Horton’s Tim Bits… they have these pumpkin filled donuts..but these look like pumpkin filled timbits- mmmmmm <3

  9. Angela says:

    I made this earlier today, and only four ended up in the oven. The batter and filling mixed together is mind-blowing.

    1. Chocolate-Covered Katie says:

      I KNEW I couldn’t be the only one who liked the raw dough so much ;).

  10. Tara says:

    A snickerdoodle cookie filled with cinnamon bun frosting would be AMAZING. Or maybe a boston creme cookie? Oh my, so many options!!

  11. Jeanna says:

    Mmm cherry filling. That would be yummy with chocolate!!!

  12. Anna says:

    Oh my! These look delicious 🙂

  13. Hannah says:

    How is it possible for a stuffed cookie to be so cute? Salted caramel version next, please? 😀

  14. Galen @ OMGosh I'm Vegan says:

    I know I’m going to dream about these cookies tonight.

  15. Kaila @healthyhelperblog! says:

    Quite possibly the best idea you’ve ever come up with!!!!!!!!!!!!!!!!!!!!!!!!!!

  16. BroccoliHut says:

    Coconut!!