Description
Delightfully festive Milk Chocolate Stuffed Jack-O’-Lantern Cookies perfect for Halloween celebrations. These soft cookies are flavored with warm spices like cinnamon, ginger, and nutmeg, stuffed with melted milk chocolate, and finished with a toasted butter and cinnamon sugar coating for extra richness and crunch.
Ingredients
Scale
Cookie Dough
- 3 sticks (1 1/2 cups) salted butter, softened
- 1 1/4 cups light brown sugar, packed
- 1 tablespoon pure vanilla extract
- 2 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
Chocolate Filling
- 12 ounces milk chocolate, melted
Cinnamon Sugar Coating
- 2 tablespoons salted butter
- 3 tablespoons cinnamon sugar
Instructions
- Prepare the Dough: In a large mixing bowl, cream together the butter, light brown sugar, and vanilla extract until the mixture is light and fluffy, approximately 3-5 minutes. Add eggs one at a time, mixing thoroughly after each addition. Incorporate the all-purpose flour, baking soda, cinnamon, ginger, nutmeg, and salt into the mixture, beating until the dough combines and forms a cohesive ball.
- Shape the Cookies: Generously flour your work surface. Divide the dough into two equal halves and flatten each into a disk. Roll each disk out to a 1/4 inch thickness using enough flour to prevent sticking. Using a pumpkin-shaped cookie cutter, cut out cookies and transfer them carefully to a parchment-lined baking sheet. For half of the cookies, use a paring knife or smaller cookie cutter to carve eyes and a mouth to create the Jack-O’-Lantern faces. Freeze the cut cookies on the baking sheet until firm, about 15-20 minutes. Re-roll any leftover scraps to maximize dough usage.
- Bake the Cookies: Preheat the oven to 350°F (175°C). Bake the cookies on the middle rack for 8-12 minutes, just until the edges are lightly golden to maintain softness inside. Avoid overbaking. Let cookies cool on the baking sheet for 5 minutes, then transfer them to a wire cooling rack to cool completely.
- Prepare Cinnamon Sugar Coating: In a medium pot, melt the 2 tablespoons of salted butter over medium heat. Continue heating until the butter starts to brown slightly and gives off a toasted aroma, approximately 2-3 minutes, stirring frequently to prevent burning. Remove from heat and allow to cool for 5 minutes. Brush this browned butter over the top halves of the cookies (the ones with faces) and immediately sprinkle with cinnamon sugar for extra flavor and a crispy finish.
- Assemble the Cookies: Spread melted milk chocolate generously over the bottom halves of the cookies (those without faces). Place the Jack-O’-Lantern face cookies on top of the chocolate-covered halves, pressing gently to adhere. These cookies can be served right away or allowed to sit until the chocolate firms up. Store in an airtight container for up to 3 days to maintain freshness.
Notes
- Recommended to use pumpkin-shaped cookie cutters for authenticity and festive appearance.
- If a pumpkin cookie cutter is unavailable, cut 3-inch circles and carve eyes and mouths manually with a sharp paring knife.
- Be careful not to overbake cookies to keep them soft and tender.
- Allow browned butter to cool slightly before brushing to avoid melting the cinnamon sugar coating immediately.
Nutrition
- Serving Size: 1 cookie
- Calories: 210
- Sugar: 14g
- Sodium: 110mg
- Fat: 12g
- Saturated Fat: 7g
- Unsaturated Fat: 4g
- Trans Fat: 0.2g
- Carbohydrates: 25g
- Fiber: 1g
- Protein: 3g
- Cholesterol: 40mg
