Milk Chocolate Stuffed Jack-O-Lantern Cookies: The Ultimate Halloween Treat!

Photo byNaomi Madison

With Halloween just around the corner, it’s time to get creative in the kitchen. What better way to embrace the spooky season than with Milk Chocolate Stuffed Jack-O-Lantern Cookies? These delightful treats bring the warmth of autumn spices and the rich creaminess of milk chocolate together in one adorable, festive cookie. Whether you’re hosting a party or simply craving a sweet snack to celebrate the holiday, these cookies are the perfect way to satisfy your seasonal sweet tooth.

A Halloween Cookie with a Twist

These cookies are more than just a pretty face. Shaped like pumpkins and filled with gooey milk chocolate, they’re a blend of fall flavors like cinnamon, nutmeg, and ginger, wrapped in a buttery, soft cookie dough. The jack-o-lantern cut-outs add a whimsical touch, making them both tasty and visually festive. It’s a cookie that both kids and adults can enjoy, and they’re as fun to make as they are to eat!

The process starts by mixing up a spiced cookie dough and rolling it out to just the right thickness. Using a pumpkin-shaped cookie cutter, you can cut out your cookie bases. For an extra spooky touch, carve jack-o-lantern faces into half of the cookies, which will become the top layer once they’re filled with melted chocolate. After baking them to a perfect golden-brown, they’re ready to be assembled with a rich, chocolate filling and a final dusting of cinnamon sugar.

Milk Chocolate Stuffed Jack-O-Lantern Cookies Recipe

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

Instructions:

1. Prepare the Dough: In a large bowl, cream together the softened butter, brown sugar, and vanilla extract until light and fluffy, about 3-5 minutes. Beat in the eggs one at a time, making sure each is fully incorporated before adding the next. Add the flour, baking soda, cinnamon, ginger, nutmeg, and salt, mixing until a smooth dough forms.
2. Roll and Cut the Cookies: Flour your work surface and divide the dough in half. Flatten each half into a disk and roll the dough out to about 1/4-inch thickness. Using a pumpkin-shaped cookie cutter, cut out cookies and transfer them to a parchment-lined baking sheet. For half of the cookies, carefully cut out jack-o-lantern faces using a pairing knife or smaller cookie cutter. Place the cookies in the freezer for 15-20 minutes to firm up before baking.
3. Bake the Cookies: Preheat your oven to 350°F (175°C). Bake the cookies on the middle rack for 8-12 minutes, or until lightly golden around the edges. Allow them to cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.
4. 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 the top of the jack-o-lantern face cookies with the browned butter and dust with cinnamon sugar.
5. Assemble the Cookies: Spread the melted milk chocolate over the flat pumpkin cookies (the ones without the faces). Gently place the jack-o-lantern face cookies on top, pressing slightly to adhere. Let the chocolate set before serving, allowing the cookies to firm up and become irresistibly delicious.

A Treat Everyone Will Love

These Milk Chocolate Stuffed Jack-O-Lantern Cookies are the perfect way to bring some Halloween cheer to your dessert table. The soft, spiced cookie paired with the rich milk chocolate filling creates a combination that’s hard to resist. Whether you're baking for your family, sharing with friends, or simply treating yourself, these cookies capture the spirit of the season in every bite. Not only do they taste great, but they’re also sure to put a smile on anyone’s face with their cute jack-o-lantern design.

Sources:

• King Arthur Baking – Spice Cookie Tips
• AllRecipes – How to Melt Chocolate
• Serious Eats – Cookie Baking Guide