Every Halloween, I love to bake a treat that’s equal parts spooky and sweet, and these Milk Chocolate Stuffed Jack-O’-Lantern Cookies are my absolute crowning achievement. They are more than just a cookie; they’re a fun, interactive project that ends in the most delicious way possible. The magic is in the surprise a hidden layer of molten milk chocolate sandwiched between two perfectly spiced, chewy brown sugar cookies.
You are going to have so much fun making and eating these cookies. The dough itself is a dream, warmly spiced with cinnamon and nutmeg, creating the perfect autumnal flavor. Cutting out the little pumpkin faces and then filling them with a gooey chocolate center is a delight for bakers of all ages. They are the ultimate Halloween treat, guaranteed to bring a smile to everyone’s face.
The Ingredients for Your Spooky Cookies
- 1 cup unsalted butter, softened.
- 1 cup granulated sugar.
- 1 cup packed brown sugar.
- 2 large eggs.
- 1 tsp vanilla extract.
- 3½ cups all-purpose flour.
- 1 tsp baking powder.
- ½ tsp baking soda.
- ½ tsp salt.
- ½ tsp ground cinnamon.
- ½ tsp ground nutmeg.
- ½ cup milk chocolate chips or chunks (for dough).
- 1 cup milk chocolate chips or chunks (for filling).
- Orange icing (for decoration).
- Black icing (for decoration).
How to Create Your Jack-O’-Lantern Cookies
Step 1: Make the Spiced Cookie Dough
In a large bowl, cream together the softened butter, granulated sugar, and brown sugar until light and fluffy. Beat in the eggs one at a time, followed by the vanilla extract. In a separate bowl, whisk together the flour, baking powder, baking soda, salt, cinnamon, and nutmeg. Gradually add the dry ingredients to the wet ingredients, mixing until just combined. Gently fold in the ½ cup of milk chocolate chips.
Step 2: Chill and Roll the Dough
Divide the dough in half, wrap each half in plastic wrap, and chill in the refrigerator for at least 1 hour. This is a crucial step to make the dough easy to roll. Once chilled, preheat your oven to 375°F (190°C) and line baking sheets with parchment paper. On a lightly floured surface, roll out one half of the dough to about ¼-inch thickness.
Step 3: Cut and Bake the Cookies
Use a pumpkin-shaped cookie cutter to cut out the cookies. On half of the pumpkins, use a small knife or mini cookie cutters to cut out Jack-O’-Lantern faces. Place all the cookies on the prepared baking sheets. Bake for 8-10 minutes, or until the edges are lightly golden. Let them cool on the baking sheet for a few minutes before transferring to a wire rack to cool completely.
Step 4: Stuff, Decorate, and Assemble
Once the cookies are cool, melt the 1 cup of milk chocolate chips for the filling in the microwave in 30-second intervals until smooth. Take a solid pumpkin cookie (without a face) and spread a layer of the melted chocolate on top. Gently place a Jack-O’-Lantern-faced cookie on top to create a sandwich. Use the orange and black icing to outline the pumpkins and fill in the facial features for extra detail, if desired. Let the chocolate set before serving.
My Best Tips for These Jack-O’-Lantern Cookies
My Secret for Perfect Cut-Outs
Chilling the dough is non-negotiable. Cold dough is much less sticky and much easier to roll and cut, ensuring your pumpkin shapes are crisp and clean. I also like to chill the cut-out cookies on the baking sheet for about 15 minutes in the freezer before baking. This helps them hold their shape perfectly and prevents spreading in the oven.
Don’t Overbake the Cookies
The key to a soft, chewy cookie is to pull them from the oven when they look just slightly underdone in the center. The edges should be set and lightly golden, but the middle will still be soft. They will continue to bake on the hot cookie sheet for a few minutes after you take them out, resulting in the perfect chewy texture.
A Fun Icing Alternative
While tube icing is quick and easy, you can also make a simple royal icing for decorating. Just whisk together some powdered sugar with a tiny bit of milk and vanilla until you reach a thick but pipeable consistency. You can color it with food coloring and use it to add all sorts of fun details to your Jack-O’-Lantern faces.
Delicious Variations to Try
These Milk Chocolate Stuffed Jack-O’-Lantern Cookies are a fantastic base for all kinds of spooky creativity. You can fill them with other types of chocolate, like dark or white chocolate, or even a swirl of Nutella. For a different flavor profile, try adding a pinch of ground ginger to the cookie dough for an extra warm spice. Instead of the icing decorations, you can brush the top cookies with melted butter and sprinkle them with cinnamon sugar for a snickerdoodle-like finish.
FAQs
Can I make the dough ahead of time?
Yes! The cookie dough can be made up to 3 days in advance and stored, well-wrapped, in the refrigerator. You can also freeze the dough for up to 3 months. Just let it thaw in the refrigerator before rolling and baking.
What if I don’t have a pumpkin cookie cutter?
No problem at all! You can simply use a round cookie cutter to make circular “pumpkin” cookies. Once they are baked, you can use orange icing to cover the top and then draw on your Jack-O’-Lantern faces with black icing.
How do I store the finished cookies?
Once the chocolate filling has set, you can store the assembled cookies in an airtight container at room temperature for up to 4 days. If your kitchen is very warm, you may want to store them in the refrigerator to keep the chocolate firm, but let them come to room temperature before serving for the best flavor and texture.
Milk Chocolate Stuffed Jack-O’-Lantern Cookies
- Total Time: 100
- Yield: 30 sandwich cookies 1x
Description
These Milk Chocolate Stuffed Jack-O’-Lantern Cookies are the ultimate Halloween treat. This fun, interactive recipe features a warmly spiced, chewy brown sugar cookie that sandwiches a hidden layer of molten milk chocolate. Decorated with festive Jack-O’-Lantern faces, these cookies are as delightful to make as they are to eat.
Ingredients
1 cup unsalted butter, softened.
1 cup granulated sugar.
1 cup packed brown sugar.
2 large eggs.
1 tsp vanilla extract.
3½ cups all-purpose flour.
1 tsp baking powder.
½ tsp baking soda.
½ tsp salt.
½ tsp ground cinnamon.
½ tsp ground nutmeg.
½ cup milk chocolate chips or chunks (for dough).
1 cup milk chocolate chips or chunks (for filling).
Orange icing (for decoration).
Black icing (for decoration).
Instructions
Make the Spiced Cookie Dough:
In a large bowl, cream together the softened butter and both sugars until light and fluffy. Beat in the eggs one at a time, then the vanilla. In a separate bowl, whisk together the flour, baking powder, baking soda, salt, cinnamon, and nutmeg. Gradually add the dry ingredients to the wet, mixing until just combined. Fold in the ½ cup of milk chocolate chips.
Chill and Roll the Dough:
Divide the dough in half, wrap each in plastic wrap, and chill for at least 1 hour. Once chilled, preheat your oven to 375°F (190°C) and line baking sheets with parchment paper. On a floured surface, roll one half of the dough to ¼-inch thickness.
Cut and Bake the Cookies:
Use a pumpkin-shaped cookie cutter to cut out the cookies. On half of the cut-outs, use a small knife or mini cutters to create Jack-O’-Lantern faces. Place all cookies on the prepared baking sheets and bake for 8-10 minutes, until the edges are lightly golden. Let them cool on the baking sheet for a few minutes before transferring to a wire rack to cool completely.
Stuff, Decorate, and Assemble:
Once cooled, melt the 1 cup of milk chocolate chips for the filling. Spread a layer of melted chocolate on a solid pumpkin cookie, then gently place a Jack-O’-Lantern-faced cookie on top to create a sandwich. Use icing to add details if desired. Let the chocolate set before serving.
Notes
Perfect Cut-Outs:
For clean shapes, chill the dough for at least an hour before rolling. For extra sharp edges, chill the cut-out cookies on the baking sheet in the freezer for 15 minutes before baking to prevent spreading.
Storage:
Store the assembled cookies in an airtight container at room temperature for up to 4 days. If the chocolate filling is soft, you can refrigerate them, but let them come to room temperature before serving for the best texture.
Filling Variations:
Feel free to get creative with the filling. You can use dark or white chocolate instead of milk chocolate, or even a swirl of Nutella for a hazelnut twist.
- Prep Time: 30
- Cook Time: 10
- Category: Dessert, Treat
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 sandwich cookie
- Calories: 210
- Sugar: 18g
- Sodium: 50mg
- Fat: undefined
- Saturated Fat: 5g
- Unsaturated Fat: 4g
- Carbohydrates: 30g
- Fiber: 1g
- Protein: 2g
- Cholesterol: 30mg
Keywords: jack-o'-lantern cookies, Halloween cookies, stuffed cookies, chocolate filled cookies, cut-out cookies, spiced brown sugar cookies
