Halloween is the perfect time for spooky treats, and there’s no better way to celebrate than with cookies that are as fun to make as they are to eat. Enter the Milk Chocolate Stuffed Jack-O-Lantern Cookies—a playful and delicious twist on classic cookie recipes. These cookies are not only adorable with their pumpkin shapes and jack-o-lantern faces, but they’re also filled with rich milk chocolate, making them a delightful surprise for anyone who takes a bite.

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With a buttery, spiced cookie base and a gooey milk chocolate center, these cookies are sure to be a hit at any Halloween gathering or fall festivity. Whether you’re hosting a party, attending a potluck, or simply looking for a festive treat to enjoy with family, these cookies offer a delicious combination of flavors and a fun presentation.

Ingredients You’ll Need

Let’s take a closer look at the ingredients that come together to make these delectable cookies.

For the Cookies:

1 1/2 cups (3 sticks) salted butter, softened: Softened butter is crucial for creating a smooth, creamy dough. It helps incorporate the sugar and gives the cookies their tender texture. Make sure the butter is at room temperature for best results.
1 1/4 cups light brown sugar, packed: Brown sugar adds a rich, caramel-like sweetness and contributes to the chewy texture of the cookies. Packing the brown sugar ensures you get the right amount for a perfect dough consistency.
1 tablespoon pure vanilla extract: Vanilla extract enhances the overall flavor of the cookies, adding a subtle but essential depth to the dough.
2 large eggs, at room temperature: Eggs bind the ingredients together and provide structure to the cookies. Using eggs at room temperature helps them mix more evenly into the dough.
4 1/2 cups all-purpose flour: Flour is the main structure-building ingredient in cookies. The amount used in this recipe ensures a sturdy dough that holds its shape while baking.
1 teaspoon baking soda: Baking soda helps the cookies rise and become light and fluffy. It reacts with the acidic ingredients in the dough to create a leavening effect.
1 teaspoon cinnamon: Cinnamon adds a warm, spicy flavor that complements the rich taste of the cookies and enhances the overall autumnal feel.
1/2 teaspoon ginger: Ground ginger provides an additional layer of spiciness, balancing the sweetness of the cookies with its aromatic warmth.
1/4 teaspoon nutmeg: Nutmeg rounds out the spice blend, adding a hint of earthiness and complexity to the cookies.
1/2 teaspoon salt: Salt intensifies the flavors in the dough and balances the sweetness of the sugar and chocolate.
12 oz milk chocolate, melted: The star of the show, milk chocolate, is melted and spread over the cookies to create a delicious, gooey center.

Directions for Making Milk Chocolate Stuffed Jack-O-Lantern Cookies

Follow these detailed steps to create your Milk Chocolate Stuffed Jack-O-Lantern Cookies. Each stage is designed to ensure that your cookies turn out perfectly every time.

Step 1: Prepare the Dough

Cream the Butter and Sugar:
- In a large mixing bowl, cream together the softened butter, light brown sugar, and vanilla extract. Use an electric mixer on medium speed and beat the mixture until it’s light and fluffy. This process should take about 3-5 minutes. The texture should be smooth, with the sugar fully incorporated into the butter.
Add the Eggs:
- Add the eggs, one at a time, mixing well after each addition. Ensure each egg is fully combined before adding the next. This helps to create a uniform dough and prevents any lumps from forming.
Combine the Dry Ingredients:
- In a separate bowl, whisk together the flour, baking soda, cinnamon, ginger, nutmeg, and salt. This step ensures that the leavening agents and spices are evenly distributed throughout the flour.
Mix the Dry Ingredients into the Wet Ingredients:
- Gradually add the dry ingredients to the creamed butter mixture, mixing on low speed until a dough forms. Avoid overmixing, as this can lead to tough cookies. The dough should come together and be slightly sticky but manageable.

Step 2: Roll and Cut the Cookies

Prepare the Work Surface:
- Generously flour your work surface to prevent the dough from sticking. Divide the dough in half and flatten each half into a disk shape. This makes rolling out the dough easier and more manageable.
Roll Out the Dough:
- Roll out each disk of dough to about 1/4-inch thickness. Use a rolling pin dusted with flour to prevent sticking. If the dough becomes too soft, refrigerate it for a few minutes to firm up.
Cut Out the Cookies:
- Use a pumpkin-shaped cookie cutter to cut out the cookies from the rolled dough. Transfer the cutouts to a parchment-lined baking sheet, arranging them about 1 inch apart. For half of the cookies, use a smaller cutter or a pairing knife to cut out jack-o-lantern faces, creating fun designs for the top layer of the sandwich.
Freeze the Cookies:
- Place the baking sheet with the cookies in the freezer for 15-20 minutes. Freezing the cookies helps them hold their shape during baking and prevents the decorations from spreading.

Step 3: Bake the Cookies

Preheat the Oven:
- Preheat your oven to 350°F (175°C). This ensures that the cookies bake evenly and achieve a golden color.
Bake the Cookies:
- Bake the cookies on the middle rack of the preheated oven for 8-12 minutes. They should be lightly golden around the edges. Keep an eye on them to prevent overbaking, as you want them to remain soft in the center.
Cool the Cookies:
- Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely. This helps them set and makes them easier to handle.

Step 4: Prepare the Cinnamon Sugar Topping

Brown the Butter:
- In a small pan over medium heat, melt 2 tablespoons of butter until it turns a light golden brown and develops a toasted aroma, about 2-3 minutes. Be careful not to burn it—watch closely as it changes color.
Brush and Dust:
- Let the browned butter cool slightly. Brush it over the top of the jack-o-lantern face cookies, then dust with cinnamon sugar. The brown butter adds a nutty flavor that complements the cinnamon sugar topping beautifully.

Step 5: Assemble the Cookies

Spread the Melted Chocolate:
- Melt the milk chocolate in a heatproof bowl over a pot of simmering water, or in the microwave in 30-second intervals, stirring in between. Once melted, spread a generous layer of chocolate over the flat (non-face) cookies.
Create the Sandwiches:
- Gently place the jack-o-lantern face cookies on top of the chocolate-covered cookies, pressing lightly to adhere. This creates a delightful stuffed cookie with a gooey chocolate center.
Let the Chocolate Set:
- Allow the assembled cookies to sit at room temperature or in the refrigerator until the chocolate has fully set. This step ensures the chocolate firms up and holds the cookies together.

Tips and Tricks for Perfect Cookies

To ensure your Milk Chocolate Stuffed Jack-O-Lantern Cookies turn out perfectly, keep these tips in mind:

Use Room Temperature Ingredients: For the best texture, make sure the butter and eggs are at room temperature. This helps them mix more evenly into the dough.
Don’t Overmix: When combining the dry ingredients with the wet, mix just until combined. Overmixing can result in tough cookies.
Chill the Dough: If the dough becomes too soft while rolling, refrigerate it for a few minutes. This makes it easier to handle and cut into shapes.
Watch the Baking Time: Every oven is different, so keep an eye on the cookies as they bake. They should be golden around the edges but still soft in the center.
Experiment with Fillings: While milk chocolate is delicious, you can experiment with other types of chocolate or even flavored fillings, like peanut butter or caramel, for a unique twist.