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. Sarahishealthy says:

    I’ve made these three times now! I think I’ll still be making them when it’s 100 degrees out!

  2. CarmenBerkey says:

    Ok I know i’ve commented on these before but I love them that much!!! I just need some more tips on making them! My pumpkin doesn’t fluff up like yours, making my cookies flat with no ‘innards’. How big of dough peices are you making that give you room to cover the pumpkin? Thank you!! I appreciate your patience with my cooking issues. 🙂 Love them!!

    1. Chocolate-Covered Katie says:

      I make pretty tiny pumpkin balls. In fact, I just put a tiny amount in the middle (not even rolling the pumpkin filling into a ball… it’s not firm enough to roll a ball, actually). What flour are you using?

      1. CarmenBerkey says:

        I was using spelt but i’m gonna switch to the white flour. It’s more of the filling that i have trouble with too…it’s really runny like pancake batter. Hmm….I use Organic pie filling from a can. What do you use? I did buy some canned pumpkin so maybe that will be better?

        1. Chocolate-Covered Katie says:

          Nope, I used organic pumpkin too. So weird that your filling is runny :-?. It’s just pumpkin mixed with pb and cinnamon, so it shouldn’t be runny at all. Sorry I can’t seem to be more helpful… I don’t know what could be wrong!

          1. CarmenBerkey says:

            i’ll keep trying!! thanks for the quick responses!!! 😉

  3. Liz says:

    Holy yum! These were so good! My mom took some to work, and everyone wanted the recipe :). Ill definitely be making them again.

  4. Brittany @ Pretty Fit, Pretty Healthy, Pretty Happy says:

    Holy mother of pearl… these look delicious. I have a long-distance baking buddy that I exchange goodies with, so I’ll have to send her some of these!!

  5. Ashley says:

    OH MY GOSH KATIE!! I just saw this recipe on Shape.com 10 healthy recipes for fall. I thought “wow those look like Katie’s cookies…” AND THEY ARE YOUR COOKIES!! I cant wait to try and make some!!

    1. Chocolate-Covered Katie says:

      Aww lol I hope you like them!!

  6. Mattie @ Comfy & Confident says:

    I am loving anything and everything pumpkin right now. These cookies look absolutely fabulous! I have to try them! yum yum yum.

  7. Claire says:

    I thought you might like knowing that this evening I mixed up half a batch of this cookie recipe just to eat the dough. I didn’t even turn on my oven! 🙂 I knew it was the dough that I wanted. Haha. I rolled the rest of the dough into balls, put them in parchment paper and stuck them in the freezer…cookie dough truffles??! We’ll see! 🙂

    1. Chocolate-Covered Katie says:

      Ooh Claire, we could be long-lost sisters! I kist did the same thing… only I ignored the pumpkin filling completely and used a few drops of peppermint extract. They were like thin mint truffles :).

    2. lena says:

      I thought about that as well! I ate one raw and they were just as good that way!

  8. Mary says:

    Delicious!
    May I post this recipe on my baking blog?!? (With a link back here of course!)

    ps. my dream cookie=filled with nutella!!!! 😉

    1. Chocolate-Covered Katie says:

      I would be honored, Mary!
      I do ask that people not copy the actual full recipe onto their sites. But you can definitely link back (and feel free to use any photos on my site if you wish).
      I’m so so glad you tried the cookies!

  9. Sarah M says:

    Hi, Katie! I don’t know if you’ll get this message since this post is from back in October, but I found a can of pumpkin in my pantry yesterday, and I remembered seeing these cookies back in October when you first posted them. Soooo…I made them tonight 🙂 However, because of current diet restrictions, I wanted to make them with little to no added sugar. The 1/4 cup is a lot when you are cutting it out of your diet altogether!! I decided to try an experiment.

    I took your posted recipe and made a few changes…and the results are pretty fantastic…and virtually sugar-free! Even my 2-year old daughter loves them. She ate two right after the ten minute “resting” period was over (yes, I timed it, because I knew I’d have a hard time waiting to try them!).

    Here’s what I changed, in case anyone else is looking for a lower-sugar option:

    Instead of the 1/4 cup + 2 T sugar, I used one over-ripe banana I pulled from my freezer, reheated, and mashed. Just to make sure, I put it into a measuring cup to make sure I was around 1/4 cup. Indeed, one banana is about 1/4 cup + 2 T. Because I was obviously adding more liquid, I cut out the extra 2 tsp of oil, and just used the 3 T ( used olive oil). I did use 2 T maple syrup (I ran out of agave making the nutella recipe…lol). I also omitted the vanilla, because I ran out this morning. Then, for the filling, I found that for my taste, there was WAY too much nut butter (I used almond butter), and not enough pumpkin. So, having first made it with your ratio, I added 2 1/2 extra T of pumpkin to increase the pumpkin flavor. Knowing I wasn’t using sugar for the cookie, and having run out of vanilla, I added about 1/4 tsp pumpkin pie spice on top of the called for cinnamon. I used the 1/2 packet of stevia.

    The dough was gummy, but I sprayed a cookie sheet covered in foil with non-stick spray, and that allowed me to easily flatten the dough to stuff it and then pick up the edges to wrap the filling.

    Whew! Sorry for the long post, but the results were so great I wanted to share!! Oh, and the extra filling? I saved that, because it tastes like a fantastic pumpkin butter that I plan to add to my oatmeal or spread on my vegan english muffins. 🙂 Win-win!

    1. Sarah M says:

      Oh, and I used dark chocolate cocoa powder…

    2. Chocolate-Covered Katie says:

      Are you kidding? I LOVE reading long, fun comments like yours! It makes me so happy when people use my recipe as a base and then come up with something completely their own. I love your banana cookie idea! 🙂

    3. Christy says:

      i tried your low-sugar version and it turned out really well 😀 im so happy, very delicious. amd i calculated the calories for this version and its about 60 cal per cookie. so yummy, im still craving these. well done katie and Sarah!

  10. Sondra says:

    I made these yesterday with the pumpkin filling- delicious! (I made these along side Isa’s ooey-gooey peanut butter cookies and the pumpkin oatmeal cookies, and my fiance, who loves sugar laden food said yours were the best… of course they had the unfair advantage of having chocolate in them 🙂 )

    I’m dying to make these and fill them tsubushi-an, but I’m out of sugar, would agave work?

    1. Chocolate-Covered Katie says:

      Sorry, I have no idea! But I’d love to know if you try :).

  11. Rachel says:

    I tried this one, but I used gluten-free all purpose baking four. I couldn’t get the dough thick enough to roll the cookie. I ended up adding about another 3/4 rice four, but it was still too sticky to do anything with. I wonder if it’s because of the xanthum gum in gluten free flour. It doesn’t work the same. I’m so disappointing I messed them up, because they look so delicious!

    1. Chocolate-Covered Katie says:

      I’m sorry to hear this :(. It worked with Bob’s… What mix did you use? I’ll fix my post to specifically say Bob’s gf. I am so sorry for my assumption that they’d all work the same. 🙁

  12. Julia says:

    Something went wrong, but I’m not sure what! I used Bob’s spelt flour, but the dough was more like brownie batter. I had to add at least 1/3 cup more flour before I even attempted to stick my hands in there. It never did become very doughlike, and its consistency caused the pumpkin to flatten– I only saw a thin line of the filling when I bit into the cookie. It was still delicious, though! I think I’ll try it again but actually attempt to make them into the brownies they so desperately wanted to be… maybe layer 1/2 of the batter in an 8X8, add a pumpkin layer, and then top off with the remaining batter?

    1. Chocolate-Covered Katie says:

      Hmmm…. I don’t know what could’ve happened! :-?.
      The brownie idea sounds awesome, though!!

  13. Renee says:

    Any idea how you’d do this without the sugar? And I’m assuming GF, you just use GF flour & that’s it? (New to gf.) Thanks! Your website rocks & makes me drool!

    1. sarah m says:

      scroll up just a little in the comments to see what I did…I used banana in place of sugar, but had to adjust the oil to compensate for the extra liquid the banana added. Good luck!

  14. Jennifer says:

    I am filling in the blank with LIME! Maybe a shortbread/blondie style cookie with lime filling!

  15. Hayley says:

    Just made these with coconut oil, and made them sugar-free by using Erythritol and liquid splenda. They are delissshhh. The texture seems a little gummy, but I’m not sure if that’s because I’m not used to such a thick cookie, or the effect of the non-sugar. In any case, my boyfriend loved them, and he had just finished eating a dark chocolate Toblerone bar. I think that says something!

  16. Vanessa says:

    This is my first recipe I’ve made from your site and it was delicious!!!