Ingredients:
1 1/2 cups (3 sticks) salted butter, softened
1 1/4 cups light brown sugar, packed
1 tablespoon pure vanilla extract
2 large eggs, at room temperature
4 1/2 cups all-purpose flour
1 teaspoon baking soda
1 teaspoon cinnamon
1/2 teaspoon ginger
1/4 teaspoon nutmeg
1/2 teaspoon salt
12 oz milk chocolate, melted
Directions:
Prepare the Dough:
In a large mixing bowl, cream together the softened butter, brown sugar, and vanilla extract until light and fluffy, about 3-5 minutes.
Add the eggs one at a time, mixing until well combined.
Add flour, baking soda, cinnamon, ginger, nutmeg, and salt. Mix until the dough forms a ball.
Roll and Cut the Cookies:
Generously flour your work surface and divide the dough in half.
Flatten each half into a disk and roll out the dough to about 1/4-inch thickness.
Using a pumpkin-shaped cookie cutter, cut out the cookies. Transfer the cookies to a parchment-lined baking sheet.
For half of the cookies, cut out jack-o-lantern faces using a pairing knife or smaller cookie cutter.
Freeze the cookies for 15-20 minutes to firm up.
Bake the Cookies:
Preheat the oven to 350°F (175°C).
Bake the cookies on the middle rack for 8-12 minutes, or until lightly golden around the edges.
Cool the cookies on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.
Prepare the Cinnamon Sugar Topping:
Melt 2 tablespoons of butter in a small pan over medium heat until it turns a light golden brown and gives off a toasted aroma, about 2-3 minutes.
Let cool slightly, then brush over the top of the jack-o-lantern face cookies. Dust with cinnamon sugar.
Assemble the Cookies:
Spread the melted milk chocolate over the flat (non-face) cookies.
Gently place the jack-o-lantern face cookies on top of the chocolate-covered cookies, pressing slightly to adhere.
Let the chocolate set before serving.
Prep Time: 30 minutes
Cooking Time: 15 minutes
Total Time: 45 minutes
Calories: Approx. 254 kcal per cookie
Servings: 30 cookies