Chocolate Pumpkin Filled Cookies

This post may include affiliate links.

I have a love affair with all things pumpkin. As soon as the leaves hint at the slightest change of color, I’m ready to hit the pumpkin patch. Something about those gargantuan squashes of all shapes and sizes give the bold fruit some major personality.

I remember prancing through what appeared like seemingly endless fields of pumpkins as a kid, and spending hours picking out the perfect fruit. As fun as pumpkin picking and pumpkin carving might be, pumpkin eating definitely tops my list of favorite pumpkin-related activities.

The bombastic fruit adds decadent flavor to all kinds of goodies, from pies and muffins to oatmeal and soups. But among the countless pumpkin-themed recipes out there, I’ll admit these Chocolate Pumpkin Filled Cookies top the charts.

In this brilliant recipe, the beloved and classic chocolate chip cookie takes on the popular orange squash like never before. We’re talking cookies with a chewy, chocolaty outside and a rich, creamy inside bursting with pumpkiny goodness. Just imagine sinking your teeth into a crispy cookie stuffed with a smooth, sinful filling that’ll send your taste buds to heaven. Yep, these cookies will do just that.

As indulgent as these delectable cookies might taste, they actually contain a host of clean, feel-good ingredients you don’t have to feel guilty about. First, the cookie portion of this dessert calls for superfoods like cocoa powder and coconut oil. Instead of conventional white flour, we’ve opted for whole wheat flour, a healthier, whole-grain alternative brimming with healthy complex carbs.

Meanwhile, we’ve sweetened these tasty treats with maple syrup, an unrefined, natural alternative to white sugar that contains higher levels of antioxidants, nutrients, and phytochemicals.

Coconut oil serves as a nutritious alternative to butter. Research points to its ability to lower bad cholesterol, reduce your risk of heart disease, and promote weight loss. Meanwhile, its anti fungal, antimicrobial properties make it a natural immune-system booster your body will certainly thank you for.

The luscious filling calls for fat-free cream cheese instead of full-fat kinds, sparing you and your waistline a hefty chunk of calories and fat. Along with pumpkin puree, this creamy filling also includes nutrient-rich spices like cinnamon and clove which add that zesty, fall-flavored kick.

The first time I whipped up a batch of these savory delights, my sister grabbed a piping hot cookie from the baking sheet before even giving the treats time to cool. She said the cookies’ mouthwatering aroma was too tempting to resist, and I don’t disagree. In fact, my family gobbled up the first batch within an hour, which was an impressive time window for just a few people.

Not to mention the creation process is actually super fun and gratifying. Simply:

  • Combine cookie and filling ingredients separately
  • Roll out the cookie dough on a sheet
  • Cut dough into circular shapes, and pop your cookie circles in the oven for 10 minutes.


  • Spoon a tablespoon of pumpkin filling in the center of each circle
  • Place a second cookie on top like a sandwich, and throw the tasty treats in the fridge until you’re ready for devouring.

Sounds easy enough. So invite your siblings and friends to get their hands dirty (but smelling delicious!) with you!

We promise you’ll fall in love with these devilishly good cookies. And the best part? You can savor every bit of their melt-in-your-mouth goodness without an ounce of guilt. Let us know what you think!

Chocolate Pumpkin Filled Cookies

A cookie recipe that the kids will adore!

Yields: 1 dozen cookies | Serving Size: 1 cookie | Calories: 146 | Total Fat: 7g | Saturated Fat: 6g | Trans Fat: 0g | Cholesterol: 1mg | Sodium: 149mg | Carbohydrates: 21g | Fiber: 3g | Sugar: 11g | Protein: 3g | SmartPoints (Freestyle): 7


    For the Cookies:
  • 1/2 cup cocoa powder
  • 1/3 cup maple syrup
  • 1 cup whole wheat flour
  • 1/3 cup coconut oil
  • 1 teaspoon baking soda
  • 1 teaspoon almond extract
  • 1/2 teaspoon salt
    For the Filling:
  • 1/4 cup fat-free cream cheese
  • 1/4 cup pumpkin puree
  • 1/2 cup powdered sugar
  • 1/2 teaspoon ground cinnamon
  • 1/4 teaspoon ground clove


    For the Cookies:
  1. Preheat oven to 350 degrees. Line a baking sheet with parchment paper and set aside.
  2. Combine all the ingredients in a large mixing bowl until just combined. Roll 1/4 inch thick on a lightly floured surface. Using a 2 inch round cookie cutter, cut into circles and place on the prepared baking sheet. Bake for 10 minutes. Remove from oven and cool completely.
    For the Pumpkin Filling:
  1. Combine all ingredients in a mixer and whip on medium speed until creamy. Spoon 1 tablespoon of the filling onto half of the cookies. Place a second cookie on top to make a cookie sandwich. Place in the refrigerator for 1 hour, or just until the filling begins to firm. Store covered in the refrigerator.

Like us on Facebook, or follow us on Pinterest and Instagram, for more delicious clean recipes!

free email series

5 Secrets to Transform Your Eating Habits

New tips & recipes to feel & look great!

3 Comments on "Chocolate Pumpkin Filled Cookies"

  1. Sean Mahan  December 14, 2017

    Seems easy enough, I’ll give it a try and share my thoughts later!

  2. Audrey  September 23, 2020

    Yummy I think they look look Oreos!

    • Nichole Furlong  September 23, 2020

      Let us know if you try the recipe, Audrey!


Leave a Comment

Your email address will not be published.