Milk Chocolate Stuffed Jack-O'-Lantern Cookies

These Milk Chocolate Stuffed Jack-O'-Lantern Cookies are a festive and fun treat for Halloween — with a creamy chocolate surprise in every bite. They’re easy to make, buttery, rich, and perfect for adding a spooky twist to your holiday table.

Prep Time 30

Cook Time 15

Total Time 45

Serving Size Cookies

Equipment

- Baking sheet
Parchment paper
- Mixing bowls
Pumpkin-shaped cookie cutter
Wire cooling rack
Airtight container

Ingredients

Cookie Dough:

2 1/2 cups all-purpose flour
1 teaspoon baking soda
1/2 teaspoon salt
1 teaspoon cinnamon (ground)
1/4 teaspoon nutmeg (ground)
1/4 teaspoon ginger (ground)
1 cup salted butter (ground)
1 cup light brown sugar
1/2 cup granulated sugar
2 eggs
2 teaspoons pure vanilla extract

Chocolate Filling:

6 ounces milk chocolate squares or discs

Cinnamon Sugar Coating:

1/4 cup granulated sugar
2 teaspoons ground cinnamon

Instructions

Preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper.
Roll out the cookie dough on a lightly floured surface to about 1/4 inch thick.
Use a pumpkin-shaped cookie cutter to cut out an even number of cookies.
With a small knife or another small cookie cutter, cut out jack-o'-lantern faces from half of the cookies.
Place a piece of milk chocolate in the center of each plain cookie.
Gently place a matching face cookie on top and press edges together to seal in the chocolate.
Roll each cookie in cinnamon sugar mixture for additional flavor.
Bake for 10–12 minutes or until edges are lightly golden brown.
Let cookies cool for 5 minutes on the baking sheet before transferring to a wire rack to cool completely.
Serve with a glass of cold milk or your favorite warm drink.

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