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
Tags: #halloweencookies #jackolanterncookies #milkchocolatecookies #spicedcookies #halloweenbaking #holidaytreats #chocolatestuffedcookies #festivebaking
These playful and delicious Milk Chocolate Stuffed Jack-O-Lantern Cookies are sure to be a hit at any Halloween gathering, combining the fun of seasonal shapes with the rich flavors of spiced cookie and milk chocolate!
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