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Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Delicious Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Delightful Milk Chocolate Stuffed Jack-O'-Lantern Cookies are soft, creamy, and a perfect treat for fall gatherings.
Prep Time 30 minutes
Cook Time 12 minutes
Chilling Time 20 minutes
Total Time 1 hour 2 minutes
Course Cookies
Cuisine American
Servings 24 cookies
Calories 200 kcal

Equipment

  • Mixing bowl
  • Electric mixer
  • Rolling Pin
  • Pumpkin-shaped cookie cutter
  • parchment paper
  • Baking sheet
  • wire rack
  • Medium pot

Ingredients
  

For the Cookie Base

  • 3 sticks Salted butter softened
  • 1.25 cups Light brown sugar packed
  • 1 tablespoon Pure vanilla extract
  • 2 large Eggs at room temperature
  • 4.5 cups All-purpose flour
  • 1 teaspoon Baking soda
  • 1 teaspoon Cinnamon
  • 0.5 teaspoon Ginger
  • 0.25 teaspoon Nutmeg
  • 0.5 teaspoon Salt

For the Chocolate Filling

  • 12 ounces Milk chocolate melted
  • 2 tablespoons Salted butter

For the Cinnamon Sugar Topping

  • 3 tablespoons Cinnamon sugar

Instructions
 

Step-by-Step Instructions

  • In a large mixing bowl, use an electric mixer to cream together 3 sticks of salted butter, 1 ¼ cups of light brown sugar, and 1 tablespoon of pure vanilla extract until light and fluffy, about 3-5 minutes. Add 2 room-temperature eggs, mixing in one at a time until smooth.
  • Gradually add in 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. Beat together until a soft, slightly sticky dough forms.
  • Flour your work surface, divide the dough in half, flatten each half into a disk, then roll out to ¼ inch thickness. Cut out cookies with a pumpkin-shaped cookie cutter and place on a parchment-lined baking sheet. Cut out eyes and a mouth on half of the cookies, then freeze for 15-20 minutes.
  • Preheat your oven to 350 degrees Fahrenheit. Bake the chilled cookies for 8-12 minutes until lightly golden. Cool on the baking sheet for five minutes before transferring to a wire rack.
  • Melt 2 tablespoons of salted butter in a medium pot over medium heat until browned and fragrant, about 2-3 minutes. Allow to cool for 5 minutes before brushing over the tops of cooled cookies.
  • Sprinkle 3 tablespoons of cinnamon sugar over the brushed cookies.
  • Spread melted 12 ounces of milk chocolate over the plain bottom halves of the cookies. Top with jack-o’-lantern halves and gently press to adhere. Serve immediately or allow chocolate to firm up before storing in an airtight container for up to 3 days.

Notes

Store cookies in an airtight container at room temperature for up to 3 days. For longer freshness, refrigerate for up to a week or freeze without filling for up to 2 months.

Nutrition

Serving: 1cookieCalories: 200kcalCarbohydrates: 28gProtein: 2gFat: 9gSaturated Fat: 5gPolyunsaturated Fat: 1gMonounsaturated Fat: 2gCholesterol: 30mgSodium: 150mgPotassium: 100mgFiber: 1gSugar: 10gVitamin A: 200IUCalcium: 20mgIron: 0.5mg
Keyword Baking, Dessert, fall treats, Halloween cookies, Jack-O’-Lantern, Milk Chocolate
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