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Jack-O'-Lantern Halloween Cookies

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

Prep Time
30 mins
Cook Time
30 mins
Chill Time
1 hr
Total Time
1 hr 40 mins
Servings: 18 sandwich cookies
Calories: 331 kcal
Course: Baked Goods
Cuisine: American

Ingredients

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

Instructions

    Cup of Yum
  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 1/4-inch thickness and cut out pumpkinshapes 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.    

Notes

  • 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.

Nutrition Information

Serving 1cookie Calories 331kcal (17%) Carbohydrates 42g (14%) Protein 5g (10%) Fat 16g (25%) Saturated Fat 10g (50%) Polyunsaturated Fat 5g Cholesterol 54mg (18%) Sodium 110mg (5%) Fiber 1g (4%) Sugar 19g (38%)

Nutrition Facts

Serving: 18sandwich cookies

Amount Per Serving

Calories 331

% Daily Value*

Serving 1cookie
Calories 331kcal 17%
Carbohydrates 42g 14%
Protein 5g 10%
Fat 16g 25%
Saturated Fat 10g 50%
Polyunsaturated Fat 5g 29%
Cholesterol 54mg 18%
Sodium 110mg 5%
Fiber 1g 4%
Sugar 19g 38%

* Percent Daily Values are based on a 2,000 calorie diet.