Halloween isn’t just about costumes and candy—it’s also one of the most exciting times of the year to bake. And nothing says festive quite like cookies shaped like jack-o’-lanterns with sweet surprises inside. These Milk Chocolate Stuffed Jack-O’-Lantern Cookies are a fun and delicious way to celebrate the season.
Picture buttery sugar cookies, perfectly golden and shaped like pumpkins, with mischievous jack-o’-lantern faces carved into the tops. Bite into one, and you’re met with a melty milk chocolate center that oozes like a sweet little Halloween trick. They’re fun for kids to help with, pretty enough to impress guests, and tasty enough to vanish from the cookie plate in minutes.
Whether you’re planning a Halloween party, need a bake sale showstopper, or want a cozy baking project for a fall afternoon, these cookies bring joy, flavor, and a bit of spooky flair to the table.
Why You’ll Love These Jack-O’-Lantern Cookies
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Perfect for Halloween – festive, playful, and seasonally themed
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Chocolate-filled surprise inside every bite
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Customizable designs with your own jack-o’-lantern faces
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Kid-friendly and fun to make together
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Great for gifting, parties, or holiday dessert tables
Ingredients You’ll Need
For the Sugar Cookie Dough:
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1 cup (2 sticks) unsalted butter, softened
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1 cup granulated sugar
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1 large egg
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1 teaspoon vanilla extract
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½ teaspoon almond extract (optional for extra flavor)
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2½ cups all-purpose flour
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½ teaspoon baking powder
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¼ teaspoon salt
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Orange food coloring (gel preferred for vibrant color)
For the Filling:
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½ cup milk chocolate chips or chopped milk chocolate
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2 teaspoons vegetable oil or heavy cream (for smoother melting)
For Decorating:
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Small sharp knife, pumpkin cookie cutter, and a paring knife or small fondant cutter
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Optional: edible glitter, black food gel for accents, or a dusting of powdered sugar
Equipment You’ll Need
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Mixing bowls
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Hand mixer or stand mixer
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Rolling pin
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Pumpkin-shaped cookie cutter (about 3–4 inches wide)
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Baking sheets
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Parchment paper
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Cooling rack
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Toothpick or skewer (for details)
Step-by-Step Instructions
Step 1: Make the Sugar Cookie Dough
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In a large bowl, cream the softened butter and sugar together until light and fluffy (about 2–3 minutes).
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Add the egg, vanilla extract, and almond extract (if using). Mix until combined.
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Add a few drops of orange gel food coloring and mix until evenly colored.
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In a separate bowl, whisk together the flour, baking powder, and salt.
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Gradually add dry ingredients to the wet mixture. Mix until a dough forms.
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Divide dough in half, flatten into discs, wrap in plastic wrap, and refrigerate for at least 1 hour (or up to overnight).
Step 2: Roll and Cut the Cookies
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Preheat the oven to 350°F (175°C). Line baking sheets with parchment paper.
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On a lightly floured surface, roll out one disc of dough to about ¼-inch thickness.
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Use the pumpkin cookie cutter to cut out as many shapes as possible. Re-roll scraps as needed.
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For half of the cookies, use a paring knife or small cutters to carve jack-o’-lantern faces (eyes, nose, mouth). These will be the tops.
Pro Tip: Chill the cut cookies for 10–15 minutes before baking to help them keep their shape.
Step 3: Bake the Cookies
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Place cookies about 1 inch apart on the prepared baking sheets.
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Bake for 8–10 minutes, or until edges are just beginning to turn golden.
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Let cookies cool on the baking sheet for 5 minutes before transferring to a cooling rack.
Step 4: Prepare the Milk Chocolate Filling
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While cookies cool, melt milk chocolate chips and vegetable oil (or cream) in a heatproof bowl over a saucepan of simmering water (double boiler method) or microwave in 20-second intervals, stirring in between.
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Stir until smooth and glossy.
Step 5: Assemble the Stuffed Cookies
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Take one whole cookie base and spread or pipe a small spoonful of melted chocolate in the center.
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Top with a jack-o’-lantern cutout cookie, gently pressing the edges to sandwich them together.
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Repeat with remaining cookies. Let set at room temperature or refrigerate for 10 minutes to firm up.
Decorating Tips and Ideas
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Use black food gel to outline eyes or add little “eyeliner” for extra expression.
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Dust cookies with edible glitter or shimmer powder for a magical Halloween effect.
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Add mini candy eyes inside the chocolate for a “peek-a-boo” monster effect.
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Use different expressions for each jack-o’-lantern—happy, spooky, goofy, or surprised!
Make-Ahead and Storage
Make-Ahead
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Dough can be made up to 2 days ahead and refrigerated.
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Unbaked cutouts can be frozen on a tray, then stored in a zip-top bag for baking later.
Storage
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Store assembled cookies in an airtight container at room temperature for up to 5 days.
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If your home is warm, refrigerate to prevent the chocolate from softening.
Freezing
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Baked cookies (without filling) can be frozen for up to 1 month.
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Fully assembled cookies can also be frozen—separate layers with parchment paper and thaw before serving.
Fun Variations
Pumpkin Spice Version
Add 1 teaspoon pumpkin pie spice to the dough for a warm fall flavor.
Chocolate Cookie Dough
Make a cocoa-based dough for a “dark chocolate pumpkin” with a white chocolate filling.
Candy-Stuffed Version
Instead of chocolate, add a dollop of Nutella, caramel sauce, or a mini peanut butter cup in the center.
Double-Stuffed
Add a layer of marshmallow fluff on top of the chocolate for a s’mores-style jack-o’-lantern cookie.
What to Serve With Jack-O’-Lantern Cookies
Create a full Halloween dessert spread with:
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Pumpkin cupcakes with cream cheese frosting
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Halloween popcorn balls
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Spooky chocolate bark
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Hot cocoa or mulled cider
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Ghost-shaped sugar cookies
Set them out with themed decor, black and orange napkins, and spooky serving trays for a festive table.
Frequently Asked Questions
1. Can I use store-bought dough?
Yes! Refrigerated sugar cookie dough can be rolled, cut, and used the same way. Add food coloring for effect.
2. How do I keep the shapes crisp?
Chill your cut cookies before baking and don’t overbake. This helps retain details.
3. Can I make these gluten-free?
Yes, use a 1:1 gluten-free baking flour. Add an extra tablespoon if the dough is too soft.
4. What type of chocolate is best?
Milk chocolate is classic, but dark chocolate or white chocolate also work well. Use high-quality chips or bars.
5. How long do they stay fresh?
They’re best within 3–4 days, but can last up to 5–6 days if stored properly.
A Halloween Baking Project Worth Savoring
Baking these Milk Chocolate Stuffed Jack-O’-Lantern Cookies is more than just a sweet treat—it’s a full-on Halloween activity. From mixing the dough to carving little faces and assembling each melty chocolate bite, this recipe brings joy to the process and magic to the result.
Perfect for baking with kids, making as gifts, or serving as a festive dessert, these cookies combine flavor, fun, and festivity in one adorable package. Make a batch this Halloween and watch smiles spread as people bite into their sweet surprise.
Conclusion
These jack-o’-lantern cookies bring the spirit of Halloween into your kitchen in the most delicious way. With buttery sugar cookies, expressive cut-out faces, and rich milk chocolate centers, they’re a spooky-sweet treat that’s as fun to make as it is to eat.
So, preheat your oven, grab your pumpkin cutter, and get ready to bake a Halloween cookie that’s sure to become a new seasonal favorite.
