If you’re on the hunt for a festive treat that perfectly marries Halloween fun with melt-in-your-mouth goodness, look no further than this Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe. These charming pumpkin-shaped cookies are not only adorable but deliver a delightful surprise of creamy milk chocolate nestled inside each one. With a tender, spiced dough featuring cinnamon, ginger, and nutmeg, every bite feels like a cozy autumn hug. Whether you’re baking for a party, the kids, or just because you love seasonal sweets, this recipe is a must-try that brings smiles and sweet memories in equal measure.

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

Ingredients You’ll Need

Gathering the ingredients for this Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe is refreshingly straightforward, yet each component plays an essential role. From the creamy butter providing richness, to the warm spices evoking that perfect fall vibe, every element contributes to the magic you’ll bake into your cookies.

  • Unsalted butter (1 ½ cups / 3 sticks): Room temperature butter adds the perfect creamy base and moisture to your dough.
  • Packed brown sugar (1 cup): Brings deep caramel notes and tender chewiness.
  • Granulated sugar (½ cup): Balances sweetness and helps create a slight crisp edge.
  • Large eggs (2): Bind the dough together and add richness.
  • Vanilla extract (1 tbsp): Enhances all the flavors with a warm, inviting aroma.
  • All-purpose flour (3 ¾ cups): The sturdy foundation for the dough’s structure.
  • Baking soda (1 tsp): Ensures lightness and perfect rise.
  • Ground cinnamon (1 tsp): Introduces classic fall warmth and spice.
  • Ground ginger (½ tsp): Adds a subtle zesty kick.
  • Ground nutmeg (¼ tsp): Rounds out the spice profile with earthiness.
  • Salt (½ tsp): Balances and brightens the sweetness.
  • Milk chocolate (12 oz): Your luscious surprise filling, chopped or bar pieces work great.
  • Cinnamon sugar: For dusting, adding a sweet-spicy finishing touch and crunch.

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

Step 1: Make the Dough

Begin by creaming together the butter, brown sugar, and granulated sugar until the mixture is light and fluffy—about 2 to 3 minutes. This creamy base ensures your cookies are rich and tender. Then, add the eggs one at a time, mixing well after each addition, followed by a generous splash of vanilla extract for that comforting aroma that makes your kitchen smell heavenly.

Step 2: Prepare Dry Ingredients

In a separate bowl, whisk together the all-purpose flour, baking soda, cinnamon, ginger, nutmeg, and salt. This blend of warm spices truly elevates the cookie dough to an irresistible fall flavor. Gradually incorporate the dry mixture into the wet ingredients, mixing until just combined to avoid overworking the dough. Then divide it in half, wrap each portion tightly in plastic wrap, and chill for at least 30 minutes so it firms up and becomes easier to work with.

Step 3: Preheat & Roll

While your dough chills, preheat the oven to 350°F (175°C). Lightly flour your work surface and roll out the dough to about ¼-inch thickness. This thickness is perfect for maintaining a tender bite but sturdy enough to hold the gooey filling. Using a pumpkin-shaped cookie cutter, cut out as many whole cookies as you can. For half of them, carve out those classic Jack-O’-Lantern faces with a sharp knife or smaller cutters, which will create a fun window to show the melted milk chocolate inside.

Step 4: Assemble the Cookies

Arrange the whole pumpkin-shaped cookies on a baking tray lined with parchment paper. Nestle a piece of milk chocolate in the center of each one, then carefully top with the Jack-O’-Lantern cutout cookie. Press the edges gently but firmly to seal the chocolate inside, making sure none peeks out to prevent sticking or leaking during baking. This assembly creates an adorable layered effect that’s as much fun as it is delicious.

Step 5: Bake and Finish

Bake your cookies for 10 to 12 minutes, just until the edges turn a light golden hue. This timing ensures the dough is perfectly cooked but still soft enough to give way to the creamy chocolate center. Once out of the oven, immediately dust them with cinnamon sugar—this little step adds a delightful crunch and festive sparkle. Let the cookies cool on the baking sheet for about 5 minutes before transferring them to a wire rack so they set beautifully without breaking.

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

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

Garnishes

To make your cookies truly shine, garnish them lightly with extra cinnamon sugar or even a pinch of edible glitter for a whimsical touch. Sprinkling chopped toasted nuts or festive sprinkles around your serving plate adds to the charm and invites guests to dig in. These little details turn your Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe into a centerpiece-worthy treat.

Side Dishes

Pairing these cookies with a warm beverage like spiced apple cider, chai latte, or even a creamy hot chocolate doubles the comfort factor. The spicy-sweet flavors of the dough complement warm drinks beautifully, making them perfect companions for a cozy evening. You might also offer a small scoop of vanilla ice cream for an indulgent dessert experience that your friends and family won’t forget.

Creative Ways to Present

For a playful twist, arrange your Jack-O’-Lantern cookies on a platter lined with colorful autumn leaves or in a carved-out pumpkin bowl. You can also place mini candles or fairy lights nearby to create a glowy, spooky vibe that fits any Halloween gathering perfectly. Wrapping a few cookies in cellophane tied with orange ribbon makes them ideal gifts to share the joy of this Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe with loved ones.

Make Ahead and Storage

Storing Leftovers

Once cooled completely, store your cookies in an airtight container at room temperature for up to 5 days. The soft texture combined with the gooey milk chocolate center remains delightful, perfect for quick snacks or last-minute Halloween treats. Keeping them layered between sheets of parchment paper prevents sticking and keeps each cookie looking beautiful.

Freezing

If you want to prepare your Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe ahead of time, freezing is a smart option. After baking, let them cool fully, then wrap each cookie individually in plastic wrap and place them inside a freezer-safe container or bag. They can be frozen for up to 2 months. When ready to indulge, simply thaw them overnight at room temperature to enjoy that freshly baked taste.

Reheating

To refresh your cookies after storage or freezing, warm them gently in a preheated oven at 300°F (150°C) for 5 to 7 minutes. This will help soften the dough and gently melt the milk chocolate center back to that heavenly oozy state. Avoid microwaving, as it can make the cookies soggy or cause uneven heating.

FAQs

Can I use dark chocolate instead of milk chocolate in this recipe?

Absolutely! Dark chocolate adds a richer, slightly bitter contrast to the sweet and spiced dough. Feel free to swap it in to customize the flavor to your liking.

How do I prevent the chocolate from leaking during baking?

Sealing the edges of the cookies carefully by pressing firmly is key. Also, using thicker dough and chilling it well before cutting helps keep everything intact while baking.

Can I make these cookies gluten-free?

Yes, you can use a gluten-free all-purpose flour blend as a substitute. Just be sure the blend contains xanthan gum or a similar binder for the best texture.

What’s the best way to cut out the Jack-O’-Lantern faces?

Sharp paring knives or small cookie cutters work best for precision. Take your time cutting out simple shapes like triangles for eyes and jagged mouths to replicate classic spooky looks.

Are these cookies suitable for making ahead for a party?

Definitely! They keep well stored and can be frozen too, making them a perfect make-ahead treat. Just warm before serving for that freshly baked feel.

Final Thoughts

Making the Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe is like inviting a little magic into your kitchen. The exciting reveal of melted milk chocolate inside charmingly spiced pumpkin-shaped cookies is a joy for all ages and occasions. I can’t recommend enough giving this recipe a try, especially as the leaves turn and the air feels crisp—these cookies are sure to become a seasonal favorite you’ll want to bake again and again.

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Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe

5 Stars 4 Stars 3 Stars 2 Stars 1 Star 4.4 from 55 reviews
  • Author: admin
  • Prep Time: 40 minutes
  • Cook Time: 12 minutes
  • Total Time: 52 minutes
  • Yield: 24 servings
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Description

Delightfully festive Milk Chocolate Stuffed Jack-O’-Lantern Cookies that combine a spiced butter cookie dough with a gooey milk chocolate center. Perfect for Halloween celebrations, these soft cookies feature charming pumpkin shapes with carved faces, dusted with cinnamon sugar for an extra touch of warmth and sweetness.


Ingredients

Scale

Dough Ingredients

  • 1 ½ cups (3 sticks) unsalted butter, room temperature
  • 1 cup packed brown sugar
  • ½ cup granulated sugar
  • 2 large eggs
  • 1 tablespoon vanilla extract
  • 3 ¾ cups all-purpose flour
  • 1 teaspoon baking soda
  • 1 teaspoon ground cinnamon
  • ½ teaspoon ground ginger
  • ¼ teaspoon ground nutmeg
  • ½ teaspoon salt

Filling

  • 12 oz milk chocolate, chopped or chocolate bars

Topping

  • Cinnamon sugar (for dusting)


Instructions

  1. Make the Dough: In a large bowl, beat the butter, brown sugar, and granulated sugar together until light and fluffy, about 2-3 minutes. Then add the eggs one at a time followed by the vanilla extract, mixing until the mixture is well combined.
  2. Prepare Dry Ingredients: In a separate bowl, whisk together the flour, baking soda, cinnamon, ginger, nutmeg, and salt. Gradually incorporate these dry ingredients into the wet mixture, stirring until a dough forms. Divide the dough into two halves, wrap each in plastic wrap, and chill in the refrigerator for at least 30 minutes or until firm.
  3. Preheat & Roll: Preheat your oven to 350°F (175°C). On a lightly floured surface, roll out the chilled dough to approximately ¼-inch thickness. Use a pumpkin-shaped cookie cutter to cut out as many cookies as possible. For half of these cut-outs, carve Jack-O’-Lantern faces using a sharp knife or smaller cookie cutters to create facial features.
  4. Assemble the Cookies: Arrange the uncut pumpkin cookies on a baking sheet lined with parchment paper. Place a piece of milk chocolate in the center of each uncut cookie. Top each with a Jack-O’-Lantern face cookie cut-out, gently pressing the edges to seal the chocolate inside.
  5. Bake & Finish: Bake the assembled cookies for 10-12 minutes, or until they turn lightly golden around the edges. Remove from the oven, immediately dust with cinnamon sugar, and let them cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.

Notes

  • Make sure the dough is well chilled before rolling to prevent sticking and to create clean cookie shapes.
  • Use good quality milk chocolate for the best melting and flavor experience.
  • Press the edges firmly to avoid chocolate oozing out during baking.
  • Store cookies in an airtight container to maintain softness.
  • These cookies can also be made ahead and frozen before baking for convenience.

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