These adorable Jack O' Lantern Halloween Sandwich Cookies are sure to be a hit at your Halloween gatherings! Each cookie is a fun pumpkin-shaped treat filled with creamy milk chocolate, topped with a buttery cinnamon-sugar coating. Carve out the faces for a spooky yet sweet surprise, making them the perfect Halloween dessert for kids and adults alike.

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The buttery cookie dough is easy to work with, and the result is a deliciously soft cookie that pairs perfectly with the rich chocolate filling. With their hand-carved jack-o'-lantern faces, these cookies are not only fun to make but also to eat!

Fun Fact: The History Behind the Jack-O'-Lantern!

The tradition of carving jack-o'-lanterns comes from an old Irish myth about a man named Stingy Jack, who tricked the Devil. The Irish originally carved faces into turnips to ward off evil spirits, but when they immigrated to America, they discovered that pumpkins were perfect for carving, leading to the tradition we follow today!

Storage Tips:

Store these cookies in an airtight container at room temperature for up to 3 days, or in the refrigerator for up to a week. Before serving, bring them to room temperature for the best flavor and texture.

Recipe Tips:

To ensure the cookies hold their shape while baking, be sure to chill the dough before rolling it out. When assembling, let the melted chocolate cool slightly so it thickens just enough to stick the cookies together without spilling.

Nutritional Information (Per Cookie, Based on 24 Cookies):

• Calories: 200 kcal
• Fat: 10g
• Carbohydrates: 25g
• Protein: 2g
• Sugar: 15g
• Fiber: 1g
• Sodium: 65mg

These Jack O' Lantern Halloween Sandwich Cookies are the perfect addition to your Halloween party table. Not only do they look festive, but they’re also a delicious combination of cinnamon-sugar and creamy chocolate!

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Jack O' Lantern Halloween Sandwich Cookies Recipe

Ingredients:

For the Cookies:

• 4 cups all-purpose flour
• 1 teaspoon baking soda
• ¼ teaspoon kosher salt
• 1 cup unsalted butter, softened
• 1 cup dark brown sugar, packed
• 1 tablespoon vanilla extract
• 2 large eggs

For the Filling and Topping:

• 1 tablespoon cinnamon
• ¼ cup granulated sugar
• 2 tablespoons unsalted butter, melted
• 8 ounces milk chocolate morsels

Instructions:

1. Prepare the Cookie Dough:Preheat the oven to 350°F (175°C). Line a cookie sheet with parchment paper and set aside. In a medium bowl, whisk together the flour, baking soda, and salt.
2. In a stand mixer, beat the softened butter, dark brown sugar, and vanilla extract on medium speed for 2-3 minutes until light and fluffy. Scrape down the sides of the bowl as needed.
3. Add the eggs one at a time, beating until well combined after each addition.
4. Gradually add the flour mixture into the butter mixture, mixing until just combined. Be careful not to overmix.
5. Flatten the dough into a disc, wrap it tightly in plastic wrap, and refrigerate for at least 1 hour.
6. Cut Out the Pumpkin Shapes:On a lightly floured surface, roll out the chilled dough to about ¼-inch thickness. Use a pumpkin-shaped cookie cutter to cut out the cookies.
7. Transfer the cut-out shapes to the prepared baking sheet. On half of the cookies, carve out jack-o'-lantern faces using a small, sharp knife or a cookie cutter designed for facial features.
8. Reroll the scraps of dough and repeat the process until all the dough is used.
9. Bake the Cookies:Bake for 11-13 minutes, until the edges turn golden. Allow the cookies to cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.
10. Add the Cinnamon-Sugar Topping:In a small bowl, combine the cinnamon and granulated sugar. Brush the tops of the cooled jack-o'-lantern cookies with melted butter, then sprinkle generously with the cinnamon-sugar mixture.
11. Assemble the Cookies:Melt the milk chocolate morsels in a microwave-safe bowl in 30-second intervals, stirring between each, until smooth. Spread a thin layer of melted chocolate on the base cookies (the ones without faces), then gently press the jack-o'-lantern tops onto the chocolate layer.
12. Let the cookies sit for about 30 minutes to allow the chocolate to firm up before serving.

Enjoy these fun and festive Jack O' Lantern Halloween Sandwich Cookies! Watch them disappear from your Halloween party faster than the candy in the trick-or-treat bowls!