🎉 Introduction
Halloween is the season of creativity — from costumes to candy and, of course, spooky baked treats! These Milk Chocolate Stuffed Jack-O’-Lantern Cookies are the ultimate festive dessert for anyone who loves a little trick with their treat.
Golden, buttery pumpkin-shaped cookies with adorable jack-o’-lantern faces hide a secret surprise: a gooey, melty milk chocolate center that oozes out with every bite. It’s a dessert that’s both playful and indulgent — perfect for Halloween parties, family baking sessions, or sweet gifts for friends.
These cookies look impressive but are actually super simple to make. With a few pantry staples and a touch of Halloween spirit, you can create cookies that taste as magical as they look. Let’s get baking and bring some edible pumpkins to life! 👻🍫
🧰 Equipment Needed
Here’s what you’ll need to make your Jack-O’-Lantern Cookies:
- Large mixing bowl
- Whisk or electric mixer
- Measuring cups and spoons
- Spatula
- Rolling pin
- Pumpkin-shaped cookie cutter
- Sharp paring knife (for carving faces)
- Baking sheet
- Parchment paper
- Cooling rack
🛒 Ingredients
These cookies are made from buttery sugar cookie dough stuffed with smooth milk chocolate.
🍪 Cookie Dough
- 2½ cups all-purpose flour
- ½ tsp baking powder
- ¼ tsp salt
- 1 cup unsalted butter (softened)
- 1 cup granulated sugar
- 1 large egg
- 1 tsp vanilla extract
- ½ tsp pumpkin pie spice (optional for flavor)
🍫 Filling & Decoration
- ½ cup milk chocolate chips or chopped milk chocolate
- 1 tsp vegetable oil (to melt chocolate smoothly)
- Orange food coloring or orange gel coloring (optional, for dough color)
- Powdered sugar for dusting
👩🍳 Directions
Step 1
Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper. Set them aside while you prepare the dough.
Step 2
In a medium bowl, whisk together flour, baking powder, and salt. If you’d like a hint of fall flavor, whisk in the pumpkin pie spice as well.
Step 3
In a large bowl, beat the butter and sugar together using an electric mixer until light and fluffy — about 2–3 minutes. This gives your cookies a soft, melt-in-your-mouth texture.
Step 4
Add the egg and vanilla extract to the butter mixture and continue mixing until fully combined.
Step 5
Gradually add the dry ingredients to the wet mixture, mixing on low speed until a soft dough forms. If you’d like orange-colored cookies, add a few drops of orange food coloring at this stage and mix until evenly tinted.
Step 6
Divide the dough in half, wrap each piece in plastic wrap, and chill in the refrigerator for 30 minutes. Chilled dough is easier to roll and cut cleanly.
Step 7
On a lightly floured surface, roll out one portion of dough to about ¼-inch thickness. Use your pumpkin-shaped cookie cutter to cut out an even number of shapes (each cookie will need a top and bottom).
Step 8
Place half of the pumpkin cutouts onto your prepared baking sheets. These will be the cookie bottoms.
Step 9
For the top cookies, use a small sharp knife to cut jack-o’-lantern faces — triangles for eyes, a little nose, and a grinning mouth. Have fun with it — each one can have its own personality!
Step 10
In a microwave-safe bowl, melt the milk chocolate chips with vegetable oil in 20-second intervals, stirring between each, until smooth and glossy.
Step 11
Spoon about a teaspoon of melted chocolate onto the center of each bottom cookie. Don’t spread it too close to the edges, as it will spread slightly when baking.
Step 12
Place a face-cut cookie on top of each chocolate-filled bottom cookie. Press the edges gently to seal them together — use a fork or your fingers to ensure no chocolate leaks out.
Step 13
Bake the cookies for 10–12 minutes, or until the edges are just starting to turn golden. Be careful not to overbake; they should remain soft and tender.
Step 14
Remove from the oven and let the cookies cool on the baking sheet for 5 minutes before transferring to a cooling rack. The chocolate inside will be molten, so allow them to cool slightly before handling.
Step 15
Dust lightly with powdered sugar or edible shimmer powder for a festive touch. Serve warm for gooey centers or let them cool completely for firmer, sandwich-style cookies.
🍽️ Servings & Timing
- Servings: 12–14 stuffed cookies
- Prep Time: 20 minutes
- Chilling Time: 30 minutes
- Cook Time: 12 minutes
- Total Time: About 1 hour
These cookies are perfect for Halloween parties, school treats, or edible gifts.
🧊 Storage & Reheating
– Store cookies in an airtight container at room temperature for up to 4 days.
– Refrigerate for up to 1 week to keep the filling fresh.
– Freeze unbaked cookie dough cutouts for up to 2 months. Bake directly from frozen, adding an extra 2–3 minutes to baking time.
– Reheat baked cookies for 10 seconds in the microwave if you want the chocolate center soft again.
Tip: These cookies taste incredible slightly warm with a glass of cold milk or hot cocoa!
🥄 Variations
Add a unique twist to your Jack-O’-Lantern Cookies with these fun ideas:
- Dark Chocolate Filling: Swap milk chocolate for dark chocolate for a richer, more decadent flavor.
- White Chocolate Glow: Use white chocolate and tint it green or orange for a spooky twist.
- Pumpkin Cream Filling: Mix cream cheese with powdered sugar and pumpkin puree for a seasonal stuffing.
- Crunchy Edges: Roll the dough edges in coarse sugar before baking for extra sparkle.
- Mini Pumpkins: Use a smaller cutter for bite-sized party treats.
- Spooky Faces: Try vampire fangs, winking pumpkins, or zigzag mouths for fun designs.
- Sprinkle Surprise: Add Halloween sprinkles inside with the chocolate filling for a playful crunch.
- Candy Bar Twist: Place a small square of milk chocolate or caramel-filled candy inside instead of melted chocolate.
- Nutty Center: Add a spoonful of hazelnut or almond spread for a nutty surprise.
- Color Contrast: Dye the dough black and orange for a two-toned cookie that screams Halloween.
❓ 10 FAQs
- Can I use white chocolate instead of milk chocolate?
Yes! It works perfectly and gives a fun “glow-in-the-dark” effect for Halloween. - Can I make the dough ahead of time?
Absolutely — store wrapped dough in the fridge for up to 2 days before baking. - Do I need to chill the dough?
Yes, chilling prevents the cookies from spreading too much while baking. - Can I use store-bought sugar cookie dough?
Definitely! Just roll it out and follow the same steps. - Can I freeze baked cookies?
Yes, freeze for up to 2 months and thaw before serving. - Can I use different shapes?
Of course! Try ghosts, bats, or witch hats using other cutters. - Can I add food coloring?
Yes, orange or black gel coloring gives your cookies a festive look. - How do I get clean Jack-O’-Lantern faces?
Chill the cut dough for 10 minutes before baking to help maintain sharp edges. - Can kids help with this recipe?
Definitely! They’ll love cutting faces and filling cookies with chocolate. - What’s the best way to serve them at a party?
Arrange cookies on a Halloween platter with candy corn, pumpkins, and a sprinkle of powdered sugar “dust.”
🏁 Conclusion
These Milk Chocolate Stuffed Jack-O’-Lantern Cookies are the perfect blend of fun, flavor, and festivity. From their buttery golden edges to their sweet, molten centers, every bite is a celebration of Halloween spirit.
They’re easy to make, eye-catching to serve, and guaranteed to disappear quickly from any dessert table. Whether you’re hosting a spooky bash or just baking for family, these cookies bring the taste of Halloween magic right into your kitchen.
So grab your rolling pin, carve some faces, and bake up these sweet little pumpkins that everyone — ghosts, ghouls, and humans alike — will adore!
Halloween Cookie Recipes: Milk Chocolate Stuffed Jack-O’-Lantern Cookies
Ingredients
Equipment
Method
- Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper. Set them aside while you prepare the dough.
- In a medium bowl, whisk together flour, baking powder, and salt. If you’d like a hint of fall flavor, whisk in the pumpkin pie spice as well.
- In a large bowl, beat the butter and sugar together using an electric mixer until light and fluffy — about 2–3 minutes. This gives your cookies a soft, melt-in-your-mouth texture.
- Add the egg and vanilla extract to the butter mixture and continue mixing until fully combined.
- Gradually add the dry ingredients to the wet mixture, mixing on low speed until a soft dough forms. If you’d like orange-colored cookies, add a few drops of orange food coloring at this stage and mix until evenly tinted.
- Divide the dough in half, wrap each piece in plastic wrap, and chill in the refrigerator for 30 minutes. Chilled dough is easier to roll and cut cleanly.
- On a lightly floured surface, roll out one portion of dough to about ¼-inch thickness. Use your pumpkin-shaped cookie cutter to cut out an even number of shapes (each cookie will need a top and bottom).
- Place half of the pumpkin cutouts onto your prepared baking sheets. These will be the cookie bottoms.
- For the top cookies, use a small sharp knife to cut jack-o’-lantern faces — triangles for eyes, a little nose, and a grinning mouth. Have fun with it — each one can have its own personality!
- In a microwave-safe bowl, melt the milk chocolate chips with vegetable oil in 20-second intervals, stirring between each, until smooth and glossy.
- Spoon about a teaspoon of melted chocolate onto the center of each bottom cookie. Don’t spread it too close to the edges, as it will spread slightly when baking.
- Place a face-cut cookie on top of each chocolate-filled bottom cookie. Press the edges gently to seal them together — use a fork or your fingers to ensure no chocolate leaks out.
- Bake the cookies for 10–12 minutes, or until the edges are just starting to turn golden. Be careful not to overbake; they should remain soft and tender.
- Remove from the oven and let the cookies cool on the baking sheet for 5 minutes before transferring to a cooling rack. The chocolate inside will be molten, so allow them to cool slightly before handling.
- Dust lightly with powdered sugar or edible shimmer powder for a festive touch. Serve warm for gooey centers or let them cool completely for firmer, sandwich-style cookies.
Notes
– Refrigerate for up to 1 week to keep the filling fresh.
– Freeze unbaked cookie dough cutouts for up to 2 months. Bake directly from frozen, adding an extra 2–3 minutes to baking time.
– Reheat baked cookies for 10 seconds in the microwave if you want the chocolate center soft again. Tip: These cookies taste incredible slightly warm with a glass of cold milk or hot cocoa! 🥄 Variations Add a unique twist to your Jack-O’-Lantern Cookies with these fun ideas: Dark Chocolate Filling: Swap milk chocolate for dark chocolate for a richer, more decadent flavor. White Chocolate Glow: Use white chocolate and tint it green or orange for a spooky twist. Pumpkin Cream Filling: Mix cream cheese with powdered sugar and pumpkin puree for a seasonal stuffing. Crunchy Edges: Roll the dough edges in coarse sugar before baking for extra sparkle. Mini Pumpkins: Use a smaller cutter for bite-sized party treats. Spooky Faces: Try vampire fangs, winking pumpkins, or zigzag mouths for fun designs. Sprinkle Surprise: Add Halloween sprinkles inside with the chocolate filling for a playful crunch. Candy Bar Twist: Place a small square of milk chocolate or caramel-filled candy inside instead of melted chocolate. Nutty Center: Add a spoonful of hazelnut or almond spread for a nutty surprise. Color Contrast: Dye the dough black and orange for a two-toned cookie that screams Halloween. ❓ 10 FAQs Can I use white chocolate instead of milk chocolate?
Yes! It works perfectly and gives a fun “glow-in-the-dark” effect for Halloween. Can I make the dough ahead of time?
Absolutely — store wrapped dough in the fridge for up to 2 days before baking. Do I need to chill the dough?
Yes, chilling prevents the cookies from spreading too much while baking. Can I use store-bought sugar cookie dough?
Definitely! Just roll it out and follow the same steps. Can I freeze baked cookies?
Yes, freeze for up to 2 months and thaw before serving. Can I use different shapes?
Of course! Try ghosts, bats, or witch hats using other cutters. Can I add food coloring?
Yes, orange or black gel coloring gives your cookies a festive look. How do I get clean Jack-O’-Lantern faces?
Chill the cut dough for 10 minutes before baking to help maintain sharp edges. Can kids help with this recipe?
Definitely! They’ll love cutting faces and filling cookies with chocolate. What’s the best way to serve them at a party?
Arrange cookies on a Halloween platter with candy corn, pumpkins, and a sprinkle of powdered sugar “dust.” 🏁 Conclusion These Milk Chocolate Stuffed Jack-O’-Lantern Cookies are the perfect blend of fun, flavor, and festivity. From their buttery golden edges to their sweet, molten centers, every bite is a celebration of Halloween spirit. They’re easy to make, eye-catching to serve, and guaranteed to disappear quickly from any dessert table. Whether you’re hosting a spooky bash or just baking for family, these cookies bring the taste of Halloween magic right into your kitchen. So grab your rolling pin, carve some faces, and bake up these sweet little pumpkins that everyone — ghosts, ghouls, and humans alike — will adore!
