Milk Chocolate Stuffed Jack-O’-Lantern Cookies – Easy & Fun Recipe

Indulge in the sweet, spiced, and perfectly chocolate-filled Milk Chocolate Stuffed Jack-O’-Lantern Cookies that will be the highlight of your fall treats. These cookies feature soft, cinnamon-spiced brown sugar cookies with a luscious milk chocolate center, making them perfect for Halloween, Thanksgiving, or any occasion when you need a cozy, chocolatey dessert. Their charming jack-o’-lantern shape adds an extra touch of fun and spookiness, ideal for sharing with family and friends.

Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Why You’ll Love These Milk Chocolate Stuffed Jack-O’-Lantern Cookies

These cookies are not only delicious but also incredibly easy to make. With a comforting blend of cinnamon, ginger, and nutmeg, the dough is spiced just right, making each bite warm and satisfying. The milk chocolate filling is the star of the show, creating a gooey, melt-in-your-mouth experience that pairs beautifully with the spiced cookies. Whether you’re celebrating Halloween, enjoying a cozy fall evening, or simply in need of a chocolate fix, these cookies will quickly become a favorite.

Ingredients for Milk Chocolate Stuffed Jack-O’-Lantern Cookies

• Salted Butter: Adds a rich, creamy texture to the dough.
• Light Brown Sugar: Provides sweetness and enhances the spice flavors.
• Pure Vanilla Extract: For a warm, aromatic base flavor.
• Eggs: Help bind the dough and contribute to its soft texture.
• All-Purpose Flour: The main structure for the cookies.
• Baking Soda: Helps the cookies rise and become soft.
• Ground Cinnamon: Adds warmth and depth to the cookie’s flavor.
• Ground Ginger: Offers a slightly spicy, earthy note.
• Ground Nutmeg: A hint of nutmeg adds a comforting, festive taste.
• Salt: Balances out the sweetness and spices.
• Milk Chocolate: The perfect filling for a gooey center.

Alternative Ingredient Suggestions

If you’re looking to make these cookies a bit lighter or cater to specific dietary needs, here are a few swaps:

Gluten-Free: Use a gluten-free flour blend to make these cookies gluten-free.
Dairy-Free: Swap out the butter for a dairy-free option like coconut oil or margarine, and use dairy-free chocolate.
Spicy Twist: Add a pinch of cayenne pepper or chili powder to the dough for a spicy kick.

Step-by-Step Instructions for Milk Chocolate Stuffed Jack-O’-Lantern Cookies

  1. Begin by preheating your oven to 350°F (175°C). Line a baking sheet with parchment paper for easy cleanup.
  2. In a large mixing bowl, cream together the softened salted butter, light brown sugar, and vanilla extract until the mixture is light and fluffy, about 3-5 minutes.
  3. Add the eggs one at a time, mixing well after each addition.
  4. In another bowl, combine the all-purpose flour, baking soda, cinnamon, ginger, nutmeg, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until a dough forms.
  5. Divide the dough in half and flatten each half into a disk. Roll out the dough to a thickness of 1/4 inch. Use a pumpkin-shaped cookie cutter to cut out your cookie shapes.
  6. Place half of the cookies on a parchment-lined baking sheet. Cut out eyes and a mouth on these using a sharp knife or cookie cutter.
  7. Place the baking sheet in the freezer and chill the cookies for 15-20 minutes until firm.
  8. While the cookies chill, melt the milk chocolate in a microwave-safe bowl or using a double boiler.
  9. Once chilled, bake the cookies for 8-12 minutes, or until the edges are lightly golden. Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a wire rack.
  10. In a small saucepan, melt butter over medium heat until browned, about 2-3 minutes. Remove from heat and let cool for 5 minutes. Brush the browned butter over the top of the cookie halves. Sprinkle with cinnamon sugar.
  11. To assemble, spread a generous amount of melted milk chocolate over the plain cookies. Place the cookie halves with the faces over the chocolate and gently press them together. Allow the chocolate to firm up before serving.
Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Tips & Tricks for Perfect Milk Chocolate Stuffed Jack-O’-Lantern Cookies

  • Chill the Dough: Chilling the dough helps prevent the cookies from spreading too much while baking and gives them a chewy texture.
  • Don’t Overbake: For soft cookies, keep an eye on the baking time. Overbaking will result in firmer, less chewy cookies.
  • Make Them Spooky: Imperfect jack-o’-lantern faces add a spooky charm to these cookies. Embrace the uneven edges for a more whimsical look.
  • Storing Leftovers: Store leftover cookies in an airtight container at room temperature for up to 3 days. For longer storage, freeze them for up to 3 months.

Pairing Ideas and Variations for Milk Chocolate Stuffed Jack-O’-Lantern Cookies

These cookies are fantastic on their own but can also be paired with a variety of beverages and treats for a festive fall spread:

• Serve with a hot cup of apple cider or pumpkin spice latte for the ultimate autumn snack.
• Add a scoop of vanilla ice cream between two cookies for a decadent dessert sandwich.
• Try adding a dash of orange zest to the dough for a citrusy twist that complements the spiced flavor.

Perfect for Fall Festivities

Milk Chocolate Stuffed Jack-O’-Lantern Cookies are ideal for your Halloween party or Thanksgiving gathering. Their charming appearance and irresistible flavor will have everyone reaching for seconds. You can also use them as a fun, personalized gift for friends and family during the fall season. With a little creativity, these cookies can be the perfect treat for any occasion.

These soft, spiced cookies filled with gooey milk chocolate are bound to become a seasonal favorite, perfect for creating lasting memories with every bite. Enjoy them fresh out of the oven or stored for later—either way, they’ll be a crowd-pleaser!

Conclusion

Milk Chocolate Stuffed Jack-O’-Lantern Cookies are the perfect balance of rich chocolate, spiced cookie dough, and a playful Halloween-inspired design. Whether you’re celebrating the spooky season or simply indulging in a delicious fall treat, these cookies bring both flavor and fun to your dessert table. The combination of a soft, cinnamon-spiced brown sugar cookie and gooey milk chocolate is sure to please everyone. Don’t forget to share these with friends and family—they’ll be asking for more after just one bite!

Frequently Asked Questions (FAQs)

Can I use dark chocolate instead of milk chocolate for the filling?

Absolutely! If you prefer a more intense chocolate flavor, feel free to swap out the milk chocolate for dark chocolate. It will give the cookies a slightly different, richer taste that’s still delicious.

How do I store Milk Chocolate Stuffed Jack-O’-Lantern Cookies?

Store your cookies in an airtight container at room temperature for up to 3 days. If you want to keep them longer, you can freeze the cookies for up to 3 months. Just make sure to place a piece of parchment paper between the layers to prevent sticking.

Can I make these cookies ahead of time?

Yes! You can prepare the cookie dough a day or two in advance. Just wrap it in plastic wrap and store it in the refrigerator until you’re ready to roll it out and bake. You can also assemble the cookies and freeze them before baking if you want to make them ahead of time.

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Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Milk Chocolate Stuffed Jack-O’-Lantern Cookies

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  • Author: Molly
  • Prep Time: 30 minutes
  • Cook Time: 15 minutes
  • Total Time: 45 minutes
  • Yield: 30 cookies 1x
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian

Description

Milk Chocolate Stuffed Jack-O’-Lantern Cookies are soft, spiced brown sugar cookies with a rich, gooey milk chocolate center. These cookies are perfect for Halloween or any fall occasion. The cinnamon, ginger, and nutmeg in the dough give the cookies a warm, spiced flavor that pairs perfectly with the sweet milk chocolate filling. A sprinkle of cinnamon sugar on top adds a little extra touch of sweetness.


Ingredients

Scale
  • 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 ground cinnamon
  • 1/2 teaspoon ground ginger
  • 1/4 teaspoon ground nutmeg
  • 1/2 teaspoon salt
  • 12 ounces milk chocolate, melted

Instructions

  1. Preheat oven to 350°F (175°C) and line a baking sheet with parchment paper.
  2. In a large mixing bowl, cream together the butter, brown sugar, and vanilla extract until light and fluffy, about 3-5 minutes.
  3. Add the eggs one at a time, mixing well after each addition.
  4. In a separate bowl, combine flour, baking soda, cinnamon, ginger, nutmeg, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until a dough forms.
  5. Divide the dough into two halves and flatten each half into a disk. Roll out the dough to about 1/4 inch thickness on a floured surface.
  6. Use a pumpkin-shaped cookie cutter to cut out the cookies. Place half of the cookies on a parchment-lined baking sheet and cut out faces (eyes and a mouth) using a knife or smaller cutter.
  7. Freeze the cookies for 15-20 minutes to firm up the dough.
  8. While the dough chills, melt the milk chocolate in a microwave-safe bowl or double boiler.
  9. Bake the cookies for 8-12 minutes, or until they are lightly golden brown around the edges. Allow them to cool on the baking sheet for 5 minutes before transferring to a wire rack.
  10. In a small saucepan, brown the butter over medium heat, stirring constantly for about 2-3 minutes. Remove from heat and let it cool for 5 minutes.
  11. Brush the browned butter over the top half of the cookies, then sprinkle them with cinnamon sugar.
  12. Spread the melted milk chocolate over the bottom half of the cookies without faces, then sandwich with the decorated top halves. Press gently to adhere and allow the chocolate to firm up before serving.

Notes

  • If you don’t have a pumpkin cookie cutter, you can use a round cutter and cut out faces with a sharp knife.
  • For a spicier cookie, increase the amount of cinnamon, ginger, or nutmeg to your taste.
  • If the dough is too sticky, refrigerate it for 10-15 minutes before rolling it out.
  • Store the cookies in an airtight container at room temperature for up to 3 days, or freeze for up to 3 months.

Nutrition

  • Serving Size: 1 cookie
  • Calories: 254 kcal
  • Sugar: 23g
  • Sodium: 125mg
  • Fat: 13g
  • Saturated Fat: 8g
  • Unsaturated Fat: 3g
  • Trans Fat: 0g
  • Carbohydrates: 32g
  • Fiber: 1g
  • Protein: 2g
  • Cholesterol: 30mg

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