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Milk Chocolate Stuffed Jack-O'-Lantern Cookies

Delightfully decorated pumpkin-shaped cookies filled with smooth melted milk chocolate, perfect for Halloween or autumn gatherings.
Prep Time 30 minutes
Cook Time 12 minutes
Total Time 42 minutes
Servings: 24 cookies
Course: Dessert, Snack
Cuisine: American, Halloween
Calories: 200

Ingredients
  

For the cookie dough
  • 3 sticks 3 sticks (1 1/2 cups) salted butter, softened
  • 1.25 cups 1 1/4 cups light brown sugar, packed
  • 1 tablespoon 1 tablespoon pure vanilla extract
  • 2 units 2 eggs, at room temperature
  • 4.5 cups 4 1/2 cups all-purpose flour
  • 1 teaspoon 1 teaspoon baking soda
  • 1 teaspoon 1 teaspoon cinnamon
  • 0.5 teaspoon 1/2 teaspoon ginger
  • 0.25 teaspoon 1/4 teaspoon nutmeg
  • 0.5 teaspoon 1/2 teaspoon salt
For the filling and topping
  • 12 ounces 12 ounces milk chocolate, melted
  • 2 tablespoons 2 tablespoons salted butter For browning
  • 3 tablespoons 3 tablespoons cinnamon sugar For sprinkling on top

Method
 

Preparation
  1. In a large mixing bowl, cream together the softened butter, light brown sugar, and vanilla extract until light and fluffy, about 3 to 5 minutes.
  2. Add the eggs one at a time, mixing until evenly combined.
  3. Add the all-purpose flour, baking soda, cinnamon, ginger, nutmeg, and salt to the bowl and beat until combined into a dough.
Shaping the Cookies
  1. Flour your work surface generously and divide the dough in half, flattening each half into a disk shape.
  2. Roll each disk out to a thickness of 1/4 inch, ensuring the dough does not stick.
  3. Use a pumpkin cookie cutter to cut out shapes and transfer to a parchment-lined baking sheet. Cut out eyes and mouth for half of the cookies.
  4. Cover and freeze the cookie sheet for 15 to 20 minutes.
  5. Preheat your oven to 350 degrees Fahrenheit during the chilling time.
Baking
  1. Bake the cookies on the middle rack for 8 to 12 minutes, until lightly golden brown. Let them cool for five minutes, then transfer to a wire rack to cool completely.
Assembling
  1. In a medium pot, brown the 2 tablespoons of salted butter over low heat, stirring often for 2 to 3 minutes, then let cool.
  2. Brush the cooled brown butter onto the tops of the cookies and sprinkle with cinnamon sugar.
  3. Spread melted milk chocolate on the bottom halves of cookies without faces and place the top halves with faces over the chocolate, gently pressing together.
Serving and Storage
  1. Serve immediately or allow the chocolate to firm up. Store in an airtight container for up to 3 days.

Notes

These cookies can be served warm, and kids can enjoy the fun of decorating and eating them. Store in an airtight container, and consider freezing them for later enjoyment.