Milk Chocolate Stuffed Jack-O’-Lantern Cookies

These milk chocolate stuffed jack-o’-lantern cookies are festive, fun, and filled with rich, gooey chocolate. With their warm fall spices, buttery dough, and playful jack-o’-lantern cutouts, they’re perfect for Halloween gatherings or a cozy autumn treat.

Why You’ll Love This Recipe

• A festive Halloween dessert that doubles as a fun baking project

• Buttery spiced cookies with a gooey milk chocolate center

• Customizable—decorate faces however you like

• Make-ahead friendly and stores well for several days

• Fun to bake with kids or for parties

Ingredients

(Tip: You’ll find the full list of ingredients and measurements in the recipe card below.)

• 1 ½ cups (3 sticks) salted butter, softened

• 1 ¼ cups light brown sugar, packed

• 1 tablespoon pure vanilla extract

• 2 eggs, at room temperature

• 4 ½ cups all-purpose flour

• 1 teaspoon baking soda

• 1 teaspoon cinnamon

• ½ teaspoon ginger

• ¼ teaspoon nutmeg

• ½ teaspoon salt

• 12 ounces milk chocolate, melted

Cinnamon Sugar Coating

• 2 tablespoons salted butter

• 3 tablespoons cinnamon sugar

Directions

1. In a large mixing bowl, cream together butter, brown sugar, and vanilla until light and fluffy, 3–5 minutes. Add eggs one at a time, mixing until smooth.

2. Mix in flour, baking soda, cinnamon, ginger, nutmeg, and salt until dough comes together.

3. Lightly flour your work surface. Divide dough in half and flatten each half into a disk. Roll out to ¼ inch thickness. Cut out pumpkin shapes with a cookie cutter. Transfer to a parchment-lined baking sheet.

4. Cut eyes and a mouth into half the cookies using a paring knife or small cutter. Place baking sheet in the freezer for 15–20 minutes until firm. Re-roll scraps and repeat.

5. Preheat oven to 350°F (175°C). Bake cookies for 8–12 minutes until lightly golden. Cool for 5 minutes on the baking sheet, then transfer to a wire rack.

6. In a small pot, melt butter until lightly browned and nutty, 2–3 minutes. Brush over the top cookies (with faces) and sprinkle with cinnamon sugar.

7. Spread melted chocolate over the base cookies (without faces). Gently press the jack-o’-lantern face cookies on top to sandwich together. Serve immediately or allow chocolate to firm before storing.

Servings and timing

• Servings: 30 cookies

• Prep time: 30 minutes

• Cook time: 15 minutes

• Total time: 45 minutes

Variations

• Filling options: Try dark chocolate, white chocolate, or a chocolate hazelnut spread.

• Extra festive: Add orange food coloring to the dough or drizzle with melted white chocolate.

• Spice swap: Add pumpkin pie spice for more fall flavor.

• Gluten-free: Use a 1:1 gluten-free baking flour blend.

• Mini cookies: Use smaller cutters for bite-sized jack-o’-lanterns.

Storage/Reheating

Store cookies in an airtight container at room temperature for up to 3 days, or refrigerate for up to 1 week. To keep them fresh longer, freeze unfilled cookies for up to 2 months, then add the chocolate filling after thawing. These cookies are best enjoyed at room temperature.

FAQs

Do I need a pumpkin-shaped cookie cutter?

No, you can use a round cutter and carve jack-o’-lantern faces with a paring knife.

Can I make the dough ahead of time?

Yes, the dough can be prepared up to 2 days in advance and stored in the fridge.

How do I prevent the dough from sticking?

Use plenty of flour when rolling out the dough to avoid sticking.

Can I use unsalted butter instead?

Yes, just add an extra ½ teaspoon of salt to balance the flavors.

Can I make these cookies gluten-free?

Yes, substitute with a gluten-free 1:1 flour blend.

How do I keep the chocolate from leaking out?

Avoid overfilling and let the chocolate firm up before serving.

Can I use white chocolate or dark chocolate instead?

Absolutely—use your favorite chocolate for the filling.

Can I freeze the finished cookies?

Yes, but freezing may slightly change the texture of the chocolate filling.

How thick should I roll out the dough?

Roll to about ¼ inch thick for the best balance of structure and softness.

Are these cookies soft or crispy?

They’re soft and slightly chewy with a crisp sugar topping.

Conclusion

Milk chocolate stuffed jack-o’-lantern cookies are the ultimate Halloween treat—fun to bake, festive to serve, and delicious to eat. With their buttery spiced dough, gooey chocolate centers, and playful pumpkin faces, they’re sure to bring smiles to kids and adults alike. Whether for a party, trick-or-treat night, or simply a cozy autumn baking day, these cookies are a seasonal must-bake.

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