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!

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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.

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. Hannah says:

    These are AMAZING. Everything I love: pumpkin, chocolate, and peanut butter! Mmmmm!

  2. Lauren says:

    Katie do you have a suggestion for an alternative to the sugar? Could I possibly do all agave nectar or would it taste funny? Oh, and my dream cookie would be stuffed with smores! Mmmmm I could just imagine the gooey marshmallows, warm fudge, and little graham cracker bits inside of that chewy chocolate cookie!

    1. Chocolate-Covered Katie says:

      I think it would taste fine… I’m not sure about the texture, though. If you try it, do let me know how it turns out!

  3. Sophie says:

    That looks absolutely AMAZING! must try.

  4. Kate says:

    Oh my goodness I just made these…and all I can say is wow. These are going to be gone before my roommates even get home! LOVE IT. 🙂
    Also, I was out of peanut butter (weird, trust me) so I just added more pumpkin and it is still absolutely delicious.

    1. Chocolate-Covered Katie says:

      Being out of pb is the worst! It happens to me all the time, because I go through it way too fast ;). Finally, I learned I need to buy the BIG jar!

      So happy you liked the cookies!

  5. Nikita says:

    I made these last night (the only change I made was using oat flour ground from rolled oats) and they were phenomenal! My husband loved them, too and said “they are a keeper.” I can’t wait to try more filling ideas out!

  6. Marian @ marianwrites says:

    these were so good! i only got about 15 small cookies out of them (with very minimal batter-eating!) and i accidentally overcooked a bit but they were still delicious! love the spicy filling. i added extra cinnamon, nutmeg and ginger. thanks katie!

    1. cck says:

      I’m starting to think I might’ve accidentally made a double batch and not remembered… because you’re not the first person to write and say it didn’t make 20 cookies. (I make a lot of recipes all at once, so maybe I got confused??) I am so sorry for the confusion, if it is indeed my mistake… I think I need to experiment again and see if this is what happened. Ha, as if I needed an excuse to make these cookies again!

      1. Amy says:

        I have to say that I thought the recipe looked so good from the beginning, that I started OUT making a DOUBLE BATCH! And I did sample some dough, but ended up with about 33 awesome cookies. I am definitely making these again. They were FABULOUS!

        1. Chocolate-Covered Katie says:

          LOL hmmm… so maybe I didn’t miscalculate? Honestly, I could’ve sworn I made a batch with 3/4c flour, and I know I got 20 cookies out of it. But two people have now told me they could only get 15. Maybe someone snuck some raw batter from their bowls while they weren’t looking? 😉
          Just kidding… or maybe not. After all, I know I’m always guilty of eating the raw batter. Who can wait for the cookies to actually bake?!

          1. Amy says:

            Well, I have to say that at the end I had become an expert on the stuffed cookie construction, but in the beginning, well, let’s just say I had some BIG (and pumpkin bulging) cookies..plus, how can you not eat this batter? It’s the BEST (I love chocolate and salt in batter!). Happy Friday!!

          2. eValerie says:

            For whatever it’s worth: I ate no batter, and got 9 cookies when I made it.

  7. CarmenBerkey says:

    HI Katie, we love these cookies but ours seem to always turn out different then yours. They are flat. 🙁 We use whole wheat flour and organic pumpkin mix. We also doubled the recipe to get more dough and still had to make them pretty big to cover the pumpkin. Can you give me more details on what kind of flour you used and your pumpkin? Thanks Katie!! Love your blog!

    1. Chocolate-Covered Katie says:

      Thanks, Carmen!

      Just as a personal preference, I don’t recommend baking with whole-wheat flour because it’s very dense. For these, I used white-whole-wheat, but spelt would also probably work well. And as for too much pumpkin filling… well, I ATE some of my pumpkin filling, so maybe that’s why I had no problem fitting the rest in the cookies ;).

  8. Mindy says:

    So disappointed. I made TWO batches (thinking i messed up the first) and the cookies didn’t even rise! They turned out flat and crispy. Baking disaster, after I homemade the pumpkin puree too 🙁

    1. Chocolate-Covered Katie says:

      Can you please tell me exactly what specific ingredients you used? Hopefully we can figure out what you did wrong! 🙂

      1. Mindy says:

        Thanks for the speedy reply! Ingredients used:
        White flour, Ghiradelli Cocoa, Light Agave Nectar, Almond Milk, Vegetable Oil, Almond Butter

        I homemade the pumpkin puree, and I worried that maybe it was a bit more watery than the average canned pumpkin puree; however, my dough wasn’t really able to be rolled into a ball…just left chocolate all over my hands! Delicious 🙂 but that was my first inkling that maybe something was wrong. I measured everything precisely, since I’m a total baking novice. I did use my food processor to mix the ingredients, which I made sure were mixed well….

        Would love to make another batch if you have any feedback, because I have TONS of pumpkin puree left. Thanks!

        1. Chocolate-Covered Katie says:

          Unfortunately, it’s very difficult to tell someone what might’ve gone wrong when I wasn’t there :-?. I know a lot of other people have had success with the recipe, so I really don’t know what could’ve happened to yours. I’m sorry I can’t be more helpful :(.

    2. Barrie says:

      These were a disaster. Mathematically, there’s absolutely NO way the chocolate cookie part could ever make enough to cover THAT much filling.

      The cookies do not rise at all. They were the same shape when they came out as when they came in. The cookie dough is too try to really wrap around the filling. We got 12 cookies out of them, and should have probably cut that in half to have enough dough to really wrap around the filling.

      Here’s photos showing how they came out: http://imgur.com/a/cm8nc

      I would like to find a better cookie recipe and try the filling in that.

      And by the way, if you didn’t get the cookies in the oven because you kept eating the dough, don’t worry, it tastes the same before and after. It’s tasty, but messy.

      1. Chocolate-Covered Katie says:

        It sounds like you must’ve done something wrong. Perhaps tried to make them too big? If you make the amount in the recipe (the 15-20), they will rise just fine and cook completely as well. 🙂

  9. ferncrest says:

    These look great !!!!! One question…. do you grease the baking sheet?

    1. Chocolate-Covered Katie says:

      I think I was lazy and didn’t, and they still popped off ok… but you can always do it if you want to be on the safe side 🙂

  10. Alyssa Monique (payfitnessforward) says:

    katie this is super cute!!! I love this idea! I cant wait to make them! have happy halloween 🙂 xoxo

  11. melissa says:

    hi katie.
    i made these cookies and my chocolate dough was a little crumbly. I could barely get it around the pumpkin filling 🙁 How did you get yours so smooth? Mine ended up looking like folded up to-go boxes.
    Tasted so so good though!
    Thanks for all your inspiring recipes.

    1. Chocolate-Covered Katie says:

      What fflour did you use? And are there any other specifics you can give me? It’s very difficult to tell someone what might’ve gone wrong when I wasn’t there 😕

      1. melissa says:

        Of course it’s difficult 🙂 I used Whole Wheat Flour. I did add extra soy milk to make the chocolate. Maybe white flour wouldn’t absorb the oil as much.

        1. Chocolate-Covered Katie says:

          As I told another commenter earlier, I do NOT recommend regular whole-wheat flour. Also, I’ve only tried these with the white-whole-wheat, so I really can’t vouch for the results with any flours other than the ones listed in the post :(.

  12. Olivia says:

    Hey Katie,

    Just tried the cookies (they are sitting the extra ten minutes out of the oven while I type) because we were carving pumpkins and carving pumpkins required pumpkin cookies…. Anyway, followed your directions to a T and my cookie batter was very, very dry!! I ended up added at least another 2 T each of oil and coconut milk. Weird?

    Also, what do you think would happen if I subbed Tofutti cc for the peanut butter for a cream cheese pumpkin filling? Would this work or does tofutti bake funny?

    Thanks!

    1. Chocolate-Covered Katie says:

      Sorry, I don’t know. If you try it, I’d love to know. Also, what flour did you use? They’re not supposed to be dry, and I’m afraid that adding extra milk might make them gummy…

      1. Olivia says:

        White whole wheat. They turned out fine after all of the additions, but it was still super crumbly… I had to make cookie tacos because they didn’t really go into balls. I was reading the comments to see if anyone else had the same problem, but it looks like it was just me. They are super yummy though, especially if you put them in fridge and let them get cold and chewy : )

  13. Cherie says:

    Yumm! Mint sounds great, maybe something with a cashew base would work? Or more chocolate, but mint flavored in the center?!

  14. Laura says:

    These were INCREDIBLE!!!

    My new favorite cookie. Thank you so much for such genius!!! 🙂

  15. Anonymous says:

    Katie, these are SO freakin good! My roommate and I polished off an entire batch in the course of three days. And now we’re planning to make more! Seriously I think I have had dreams about these cookies, they’re so good.

    **Runs off to make more cookies!!!

  16. Barb says:

    YUM! I loved these. Thanks for a terrific recipe, yet again. I keep telling eveyone I know about your site, because it is the best site out there! Keep up the awesome work, girl!