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Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Milk Chocolate Stuffed Jack-O’-Lantern Cookies for Halloween Fun

Delightful Milk Chocolate Stuffed Jack-O’-Lantern Cookies are a perfect festive treat for Halloween gatherings with their spiced dough and creamy filling.
Prep Time 30 minutes
Cook Time 10 minutes
Chilling Time 30 minutes
Total Time 1 hour 10 minutes
Servings: 12 cookies
Course: Desserts
Cuisine: American
Calories: 250

Ingredients
  

For the Cookie Dough
  • 1.5 cups Salted Butter Can substitute unsalted butter to control salt levels.
  • 1.25 cups Light Brown Sugar Dark brown sugar can be used for a deeper flavor.
  • 1 tablespoon Pure Vanilla Extract Almond extract can be swapped for a different taste.
  • 2 pieces Eggs At room temperature; use flax eggs for a vegan alternative.
  • 4.5 cups All-Purpose Flour Substitute with a 1:1 gluten-free flour blend for gluten-free option.
  • 1 teaspoon Baking Soda Baking powder can be used as an alternative.
  • 1 teaspoon Cinnamon Nutmeg or pumpkin spice can provide a delightful twist.
  • 0.5 teaspoon Ginger Feel free to omit for less spice.
  • 0.25 teaspoon Nutmeg Substitute with allspice for a rounded flavor.
  • 0.5 teaspoon Salt Reduce slightly for a low-sodium version.
For the Filling and Topping
  • 12 ounces Melted Milk Chocolate Dark or white chocolate can be swapped based on preference.
  • 2 tablespoons Salted Butter For brushing.
  • 3 tablespoons Cinnamon Sugar Feel free to use store-bought cinnamon sugar.

Equipment

  • Mixing Bowl
  • Hand mixer
  • Whisk
  • Cookie cutter
  • Baking Sheet
  • Parchment paper
  • Refrigerator

Method
 

Step-by-Step Instructions
  1. In a large mixing bowl, combine 1 ½ cups of softened salted butter with 1 ¼ cups of light brown sugar and 1 tablespoon of pure vanilla extract. Beat the mixture on medium speed for about 3-5 minutes until light and fluffy.
  2. Add 2 room-temperature eggs, one at a time, mixing well after each addition. Blend until the batter is smooth and creamy.
  3. Whisk together 4 ½ cups of all-purpose flour, 1 teaspoon of baking soda, 1 teaspoon of cinnamon, ½ teaspoon of ginger, ¼ teaspoon of nutmeg, and ½ teaspoon of salt. Gradually add the dry mixture to the wet ingredients, mixing on low speed until a soft dough forms.
  4. Divide the dough into two halves, flatten into disks, wrap in plastic wrap, and chill in the refrigerator for about 30 minutes.
  5. Preheat your oven to 180°C (350°F). On a floured surface, roll out one disk of dough to ¼ inch thick and use a pumpkin-shaped cutter to cut out cookies.
  6. Place the cut cookies on a baking sheet lined with parchment paper and freeze for about 15-20 minutes.
  7. Bake the chilled cookies in the preheated oven for 8-12 minutes or until lightly golden. Let cool on the baking sheet for 5 minutes.
  8. Melt 12 ounces of milk chocolate and brush over the flat sides of half the cookies.
  9. Spread melted chocolate on the flat sides of the cookies and top with the decorated pieces, creating sandwiches.
  10. Brush 2 tablespoons of melted salted butter over the tops of the assembled cookies and sprinkle with 3 tablespoons of cinnamon sugar. Let set before serving.

Nutrition

Serving: 1cookieCalories: 250kcalCarbohydrates: 30gProtein: 3gFat: 12gSaturated Fat: 7gPolyunsaturated Fat: 0.5gMonounsaturated Fat: 3gCholesterol: 30mgSodium: 150mgPotassium: 100mgFiber: 1gSugar: 15gVitamin A: 200IUCalcium: 30mgIron: 1mg

Notes

For optimal texture, be sure to chill the dough and avoid overbaking the cookies for chewy perfection.

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