Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe

If you’re looking for a festive treat that’s as much fun to make as it is to eat, Milk Chocolate Stuffed Jack-O’-Lantern Cookies are the answer! These adorable pumpkin-shaped cookies are bursting with creamy milk chocolate, have a hint of warm pumpkin spice, and are decorated with playful jack-o’-lantern faces. Whether you’re baking for a Halloween party or just want to surprise your family with something special, these cookies deliver on both flavor and charm. Let’s dive into the magic of Milk Chocolate Stuffed Jack-O’-Lantern Cookies!

Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe - Recipe Image

Ingredients You’ll Need

The beauty of Milk Chocolate Stuffed Jack-O’-Lantern Cookies lies in their simple, pantry-friendly ingredients. Each one plays an important role, from creating a soft, tender dough to delivering that signature pumpkin color and cozy autumn flavor.

  • All-purpose flour: This is your cookie’s foundation, giving them structure and a perfect bite.
  • Baking powder: Helps the cookies puff up just the right amount for a soft, tender texture.
  • Salt: A tiny pinch makes all the flavors pop and balances the sweetness.
  • Unsalted butter (softened): Adds richness and helps create that classic, melt-in-your-mouth cookie texture.
  • Granulated sugar: Provides sweetness and encourages those lightly golden edges.
  • Light brown sugar (packed): Gives a subtle molasses note and helps keep the cookies chewy.
  • Large egg: Binds everything together and adds moisture.
  • Vanilla extract: Elevates all the other flavors and adds a cozy aroma.
  • Pumpkin pie spice: Brings the essence of autumn with warm, fragrant spice.
  • Orange gel food coloring (as needed): Turns your dough into the most vibrant, pumpkin-like shade.
  • Milk chocolate squares or discs (20–24): The star of the show—these create a luscious, gooey center in every cookie.
  • Mini chocolate chips or melted dark chocolate (for decoration): Perfect for drawing whimsical jack-o’-lantern faces once the cookies are baked and cooled.

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

Step 1: Mix the Dry Ingredients

Start by whisking together your flour, baking powder, salt, and pumpkin pie spice in a medium bowl. This not only ensures even distribution of the leavening and spices but also sets up your dough for perfect consistency. The pumpkin pie spice adds a subtle warmth that will make every bite feel like fall.

Step 2: Cream the Butter and Sugars

In a larger bowl, use an electric mixer to cream your softened butter with both sugars. Beat for about 2–3 minutes until the mixture is light and fluffy. This step is key for cookies that are tender and slightly chewy, with that classic bakery-style texture.

Step 3: Add Egg and Vanilla

Beat in the egg and vanilla extract until fully incorporated. The egg brings everything together, while the vanilla infuses the dough with a cozy aroma that perfectly complements the pumpkin pie spice.

Step 4: Combine and Color

Gradually add your dry ingredients to the wet mixture, mixing on low until just combined. Now for the fun part: add orange gel food coloring a little at a time, mixing until the dough is an intense pumpkin orange. This is what gives Milk Chocolate Stuffed Jack-O’-Lantern Cookies their unmistakable festive look!

Step 5: Chill the Dough

Divide the dough in half, shape into discs, and wrap each in plastic wrap. Chill for at least 30 minutes. This step makes the dough easier to roll out and helps the cookies hold their shape while baking.

Step 6: Cut Out and Assemble the Cookies

Preheat your oven to 350°F (175°C). Roll out one portion of dough on a lightly floured surface to about 1/4-inch thickness. Use a pumpkin-shaped cookie cutter for the base. For half of the cookies, use a small knife or mini cutter to make jack-o’-lantern faces. Place uncut cookies on a lined baking sheet, top each with a square of milk chocolate, then cover with a face-cut cookie. Gently press the edges to seal in that delicious chocolate.

Step 7: Bake to Perfection

Bake your assembled cookies for 10–12 minutes, just until the edges are golden but the centers are still soft. Let them cool on the pan for 5 minutes before transferring to a wire rack. This ensures they set up without becoming too crisp—unless you like them extra crunchy, in which case, bake for an extra minute or two.

Step 8: Decorate Those Faces

Once the cookies are fully cooled, use melted dark chocolate or mini chocolate chips to fill in the eyes and mouths, bringing your Milk Chocolate Stuffed Jack-O’-Lantern Cookies to life. Get creative—spooky, silly, or sweet, each face is part of the fun!

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

Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe - Recipe Image

Garnishes

For a festive finish, dust a little powdered sugar around your cookies or add a dot of green icing for a “pumpkin stem.” Even a sprinkle of edible glitter or gold dust can make your Milk Chocolate Stuffed Jack-O’-Lantern Cookies sparkle on the dessert table.

Side Dishes

Pair these cookies with mugs of hot apple cider, creamy chai lattes, or even a scoop of vanilla ice cream. The comforting flavors of autumn drinks and desserts really make the chocolate and spice in your cookies pop.

Creative Ways to Present

Arrange your Milk Chocolate Stuffed Jack-O’-Lantern Cookies on a platter lined with faux autumn leaves or nestle them in a basket for a Halloween party. You can even wrap them individually in cellophane bags tied with orange and black ribbon for adorable trick-or-treat favors.

Make Ahead and Storage

Storing Leftovers

Keep any leftover Milk Chocolate Stuffed Jack-O’-Lantern Cookies in an airtight container at room temperature. They’ll stay soft and flavorful for up to five days—if they last that long!

Freezing

These cookies freeze beautifully. Once cooled, layer them between sheets of parchment in a freezer-safe container. They’ll keep for up to two months and are perfect for making ahead before the busy holiday season.

Reheating

To enjoy that gooey chocolate center again, just pop a cookie in the microwave for about 8–10 seconds. It’s like a bakery-fresh treat all over again!

FAQs

Can I use a different type Dessert

Absolutely! While milk chocolate gives these cookies their classic creamy center, dark chocolate, white chocolate, or even caramel-filled squares are delicious alternatives.

Do I need to chill the dough?

Yes, chilling the dough helps prevent the cookies from spreading too much and makes it much easier to cut out the pumpkin shapes. It’s a small step that makes a big difference.

How do I get a vibrant orange color?

Gel food coloring is your best friend here. It gives a bold, pumpkin-like hue without adding extra liquid to your dough. Add it gradually until you reach your desired shade.

Can I make these cookies gluten-free?

You can try substituting a 1:1 gluten-free baking flour blend for the all-purpose flour. Just be sure to check the texture of your dough and adjust as needed.

What’s the best way to seal the cookies?

Press the edges gently but firmly after sandwiching the chocolate between two cookies. If needed, use a fork or your fingers to crimp the edges for extra security and a cute, rustic look.

Final Thoughts

There’s something magical about baking and sharing Milk Chocolate Stuffed Jack-O’-Lantern Cookies, whether you’re making memories with family or delighting guests at a fall gathering. They’re whimsical, chocolatey, and packed with autumn flavor—so gather your ingredients and let the cookie fun begin!

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Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe

Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe


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4.8 from 21 reviews

  • Author: admin
  • Total Time: 42 minutes
  • Yield: 1012 stuffed cookies 1x
  • Diet: Vegetarian

Description

Delightfully festive and fun, these Milk Chocolate Stuffed Jack-O’-Lantern Cookies feature soft pumpkin-colored dough encasing creamy milk chocolate centers. Perfect for Halloween celebrations, they combine warm pumpkin pie spices with sweet chocolate and are decorated with charming spooky faces, making them irresistible treats for kids and adults alike.


Ingredients

Scale

Dry Ingredients

  • 2 1/2 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon salt
  • 1/2 teaspoon pumpkin pie spice

Wet Ingredients

  • 3/4 cup unsalted butter, softened
  • 3/4 cup granulated sugar
  • 1/2 cup light brown sugar, packed
  • 1 large egg
  • 1 teaspoon vanilla extract
  • Orange gel food coloring, as needed

Filling

  • 2024 milk chocolate squares or discs (such as chocolate melts or chocolate chunks)

For Decoration

  • 1/4 cup mini chocolate chips or melted dark chocolate (for eyes and mouths)


Instructions

  1. Mix Dry Ingredients: In a medium bowl, whisk together the all-purpose flour, baking powder, salt, and pumpkin pie spice until well combined.
  2. Cream Butter and Sugars: In a large bowl, use a mixer to cream the softened unsalted butter with granulated sugar and light brown sugar until the mixture is light and fluffy, about 2–3 minutes.
  3. Add Egg and Vanilla: Beat in the egg and vanilla extract thoroughly until fully incorporated.
  4. Combine Ingredients: Gradually add the dry ingredients to the wet ingredients, mixing until a cohesive dough forms. Add orange gel food coloring a little at a time until the dough achieves a deep, vibrant pumpkin color.
  5. Chill Dough: Divide the dough into two equal portions, wrap each in plastic wrap, and refrigerate them for 30 minutes to firm up.
  6. Preheat Oven and Prepare Dough: Preheat your oven to 350°F (175°C). On a lightly floured surface, roll out one portion of dough to about 1/4-inch thickness.
  7. Cut Shapes and Faces: Use a pumpkin-shaped cookie cutter to cut out cookies. For half of these cookies, cut out jack-o’-lantern faces using a small sharp knife or mini cutters to create eyes and mouths.
  8. Assemble Stuffed Cookies: Place the uncut cookies on a parchment-lined baking sheet. On each one, place a milk chocolate square or disc. Gently top with a face-cut cookie and press the edges lightly together to seal the chocolate inside.
  9. Bake Cookies: Bake the assembled cookies for 10–12 minutes, or until the edges just start to turn golden brown.
  10. Cool and Decorate: Let the cookies cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely. Once cooled, use mini chocolate chips or melted dark chocolate to enhance facial features by piping eyes and mouths if desired.

Notes

  • For crispier cookies, bake 1-2 minutes longer, watching carefully to avoid burning.
  • Try substituting dark or white chocolate for the milk chocolate filling to experiment with flavors.
  • Store cookies in an airtight container at room temperature for up to 5 days to keep them fresh.
  • These cookies freeze well; reheat in the microwave for a few seconds to soften the chocolate filling before serving.
  • Prep Time: 30 minutes
  • Cook Time: 12 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 1 stuffed cookie
  • Calories: 260
  • Sugar: 19g
  • Sodium: 70mg
  • Fat: 13g
  • Saturated Fat: 8g
  • Unsaturated Fat: 4g
  • Trans Fat: 0g
  • Carbohydrates: 33g
  • Fiber: 1g
  • Protein: 3g
  • Cholesterol: 35mg

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