Yield: 18 sandwich cookies

Jack-O'-Lantern Halloween Cookies

Prep Time 30 minutes
Cook Time 10 minutes
Chill Time 1 hour
Total Time 1 hour 40 minutes

Jack-O'-Lantern Halloween Cookies are sure to put a smile on your face! Chewy cookies layered with milk chocolate and topped with cinnamon sugar, they're the perfect tasty treats for spooky season


For the Cookies

  • 4 cups all-purpose flour
  • 1 teaspoon baking soda
  • ¼ teaspoon kosher salt
  • 1 cup unsalted butter, softened
  • 1 cup dark brown sugar, packed
  • 1 Tablespoon vanilla extract
  • 2 large eggs

For the Filling and Topping

  • 1 Tablespoon cinnamon
  • ¼ cup granulated sugar
  • 2 Tablespoons unsalted butter, melted
  • 8 ounce milk chocolate morsels


    1. Preheat your oven to 350 degrees F. Line your cookie sheet with parchment paper and set aside.    
    2. Combine the flour, baking soda, and salt in a bowl and keep aside.   
    3. In a stand mixer (you can also use the hand mixer for this) add the softened butter, brown sugar, and vanilla. Beat at medium speed, scraping down the sides of the bowl as needed, for at least 2-3 min or until the mixture is creamy.    
    4. Add in the eggs and beat until blended into the cookie dough.    
    5. Add the flour mixture to the butter mixture in batches and mix just until the dough is formed.     
    6. Flatten the dough to form a large disc, wrap it with plastic wrap, and refrigerate for at least an hour.     
    7. Once chilled, roll out the dough on a lightly floured surface to ¼-inch thickness and cut out pumpkin
      shapes using a pumpkin cookie cutter.    
    8. Transfer the cut-out cookies carefully to the prepared baking tray and then use a sharp knife to carve out eyes and mouths as you like in half of the cookies (or use a cookie cutter that has the face shapes).
    9. Roll the leftover dough and repeat the process.    
    10. Bake in a preheated oven for 11-13 minutes or until they begin to turn golden-brown.
    11. Let the cookies cool for 5 minutes on the cookie sheet before transferring them to a wire rack to cool completely.    
    12. Combine cinnamon with sugar for the topping. Brush melted butter on top of the cooled cookies and then sprinkle cinnamon sugar on top.   
    13. Assembling - Apply a layer of the melted chocolate on the base cookie and then place the carved-out cookie on top. Press gently.    


  • Store HALLOWEEN JACK-O-LANTERN COOKIES in an airtight container for 3 days at room temperature or in the refrigerator.       
  • You can add ground cinnamon, nutmeg, ginger, and all-spice powder to the cookies for an extra kick of warm flavors. Or add a teaspoon of pumpkin pie spice to the cookie dough.
  • See blog post for more recipe tips and tricks.

Nutrition Information:



Serving Size:

1 cookie

Amount Per Serving: Calories: 331Total Fat: 16gSaturated Fat: 10gTrans Fat: 0gUnsaturated Fat: 5gCholesterol: 54mgSodium: 110mgCarbohydrates: 42gFiber: 1gSugar: 19gProtein: 5g

*Nutrition facts are an estimate and not guaranteed to be accurate. Please see a registered dietitian for special diet advice.

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