How to Make Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Looking for a festive and indulgent treat this Halloween? These Milk Chocolate Stuffed Jack-O’-Lantern Cookies offer the perfect balance of soft, buttery cookie dough and melty, rich chocolate hidden inside. Whether you’re baking with kids or planning a party, these cookies will steal the spotlight with their fun pumpkin faces and decadent centers. Get ready to fill your home with sweet aromas and smiles!

Why You’ll Love This Recipe

• Irresistible flavor: The combination of buttery cookie dough and creamy milk chocolate creates a truly heavenly bite.
• Festive design: Carving jack-o’-lantern faces makes these cookies fun to decorate and perfect for Halloween parties.
• Kid-friendly: This recipe is super approachable for little helpers to get involved with baking and decorating.
• Soft and gooey texture: The melted chocolate inside ensures every cookie stays moist and chewy.
• Great for sharing: These crowd-pleasers are ideal for gifting or passing around at gatherings.

Ingredients You’ll Need

These ingredients are simple pantry staples that come together beautifully to create the soft cookie base and luscious chocolate filling that makes these Milk Chocolate Stuffed Jack-O’-Lantern Cookies shine.

• All-purpose flour: Provides structure for the soft cookie dough without overpowering its tender crumb.
• Unsalted butter: Adds richness and moisture, giving cookies their melt-in-your-mouth softness.
• Granulated sugar: Sweetens the dough evenly and helps create a slight crisp on the edges.
• Brown sugar: Offers depth of flavor and contributes to the chewy texture with its natural molasses content.
• Egg: Binds ingredients and gives the dough a tender but sturdy consistency.
• Vanilla extract: Enhances flavor with subtle warmth and aroma.
• Baking soda: Works as a gentle leavening agent for lightness.
• Salt: Balances sweetness and intensifies all other flavors.
• Milk chocolate bars or chunks: The star ingredient, creating the gooey center in every cookie.
• Orange food coloring and black icing: Essential for decorating the jack-o’-lantern faces with vibrant Halloween flair.

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

Feel free to make this recipe your own! Whether you want to tweak the flavors, adapt to your dietary needs, or experiment with new textures, these variations are simple and fun.

• Dark chocolate center: Swap milk chocolate for dark chocolate if you prefer a richer or less sweet filling.
• Almond flour dough: Use almond flour in place of some all-purpose flour for a nutty flavor and gluten-friendly option.
• Vegan adaptation: Replace butter with coconut oil and use a flax egg to keep things plant-based.
• Spiced dough: Add cinnamon and nutmeg to the dough for a cozy pumpkin spice twist.
• White chocolate filling: Try white chocolate for a gooey, sweeter surprise inside your pumpkin cookies.

How to Make Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Step 1: Prepare the Dough

Begin by creaming together the softened unsalted butter with both granulated and brown sugar until light and fluffy. Beat in the egg and vanilla extract, ensuring everything is well combined. In a separate bowl, sift together the all-purpose flour, baking soda, and salt. Gradually add the dry ingredients to the wet mixture, stirring gently until a soft dough forms. Add a few drops of orange food coloring and mix until the dough is evenly tinted the perfect pumpkin shade.

Step 2: Shape the Cookies

Take a small scoop of dough – about one tablespoon – and flatten it slightly in the palm of your hand. Place a small piece of milk chocolate in the center, then gently fold the dough around the chocolate, sealing it completely. Roll into a smooth ball and place on a parchment-lined baking sheet. Repeat until all the dough and chocolate are used up, spacing the cookies a couple of inches apart to allow for spreading.

Step 3: Carve the Jack-O’-Lantern Faces

Using a quick-drying tool like the handle of a spoon or a toothpick, gently press or carve out simple pumpkin face shapes on the surface of each cookie. Make eyes, noses, and mouths with friendly or spooky expressions. Don’t press too hard to avoid breaking the dough, just enough to leave a clear outline.

Step 4: Bake and Cool

Preheat your oven to 350°F (175°C). Bake the cookies for 10 to 12 minutes, or until edges are just set but centers remain soft. Once out of the oven, let them cool on the tray for a few minutes before transferring to a wire rack to cool completely. This allows the milk chocolate inside to maintain its gooey texture.

Step 5: Decorate with Icing

Once cooled, use black icing to trace around the carved faces and fill in details, enhancing the spooky jack-o’-lantern look. Allow the icing to set before serving or storing.

Pro Tips for Making Milk Chocolate Stuffed Jack-O’-Lantern Cookies

• Chill the dough: Refrigerate the dough for 30 minutes if too soft to handle easily, helping with shaping.
• Seal the chocolate well: Make sure the chocolate pieces are completely wrapped in dough to prevent leaking during baking.
• Use fresh chocolate: Higher-quality milk chocolate melts better and tastes richer inside the cookies.
• Don’t overbake: Pull your cookies out as soon as edges set for soft centers and gooey chocolate.
• Experiment with faces: Mix up jack-o’-lantern expressions to add personality and fun to your batch.

How to Serve Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Garnishes

Sprinkle with a little orange sanding sugar before baking for extra sparkle, or dust lightly with powdered sugar when serving to mimic autumn frost. Add a festive touch with edible gold glitter or a few chocolate chips arranged as extra facial features.

Side Dishes

Pair these cookies with a warm cup of spiced pumpkin latte, rich hot chocolate, or chai tea for the ultimate cozy vibe. Fresh apple slices or a handful of candied pecans also complement the sweet and chocolatey flavors perfectly.

Creative Ways to Present

Display your cookies on a rustic wooden tray or a Halloween-themed platter surrounded by mini pumpkins and autumn leaves. Tie bundles of three or four with orange ribbon for adorable little gifts or package individually in clear bags with themed tags for party favors.

Make Ahead and Storage

Storing Leftovers

Keep leftover Milk Chocolate Stuffed Jack-O’-Lantern Cookies in an airtight container at room temperature, separated by parchment paper to prevent sticking. They will stay fresh and soft for up to 4 days.

Freezing

Wrap cookies tightly in plastic wrap and place in a freezer-safe bag or container. Freeze for up to 3 months, then thaw at room temperature when ready to enjoy. For best results, decorate with icing after thawing.

Reheating

Warm cookies gently in the microwave for 10 to 15 seconds to bring back that melted chocolate delight. Alternatively, reheat in a low oven (300°F/150°C) for about 5 minutes for a slightly crispier edge.

FAQs

Can I use dark chocolate instead of milk chocolate?

Absolutely! Dark chocolate adds a richer, slightly less sweet center without changing the texture much. It’s a great option if you prefer a deeper chocolate flavor.

How do I prevent the chocolate from leaking out during baking?

Make sure the chocolate is fully covered by cookie dough and sealed tightly around the edges. Chilling the dough briefly before baking can also help minimize spreading and leaks.

Can I prepare these cookies without food coloring?

Yes, you can skip the orange coloring and still have delicious cookies. The jack-o’-lantern look is fun, but the flavor and gooey center remain the star!

Are these cookies suitable for kids to help make?

Definitely! Kids will love shaping the dough, stuffing the chocolate, and especially decorating the faces. Just supervise when using sharp tools or handling the oven.

What’s the best way to decorate the faces?

Using black icing pens or piping bags with a fine tip allows for controlled, neat lines. You can also use melted chocolate and a toothpick for delicate details.

Final Thoughts

These Milk Chocolate Stuffed Jack-O’-Lantern Cookies bring the magic of Halloween straight to your kitchen with their adorable designs and melt-in-your-mouth indulgence. Whether you’re baking for family, friends, or a festive crowd, this recipe is sure to delight everyone. Go ahead, try making your own batch and experience how fun and rewarding this sweet tradition can be!

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