Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe
If you’re looking to bring some festive joy and mouthwatering flavor to your Halloween celebrations, these Milk Chocolate Stuffed Jack-O’-Lantern Cookies are an absolute must-try. Imagine tender, spiced pumpkin-shaped cookies with a rich, creamy milk chocolate center that melts in your mouth. They’re not only charmingly seasonal but also wonderfully indulgent, perfectly balancing warm autumn spices with sweet, gooey chocolate. Whether you’re baking for a party, to delight the kids, or simply craving a cozy treat, these cookies deliver everything you want in a fall dessert with a fun, festive twist.
Ingredients You’ll Need
Getting ready to bake these Milk Chocolate Stuffed Jack-O’-Lantern Cookies is simple and fun because the ingredients are all familiar pantry staples. Each one plays a special role—from the fragrant spices that give the cookies their cozy, fall flavor to the creamy butter that ensures the perfect soft texture.
- 3 sticks (1 1/2 cups) salted butter: Softened butter brings richness and tenderness to the cookie dough.
- 1 1/4 cups light brown sugar: Adds a hint of caramel sweetness and helps keep the cookies moist.
- 1 tablespoon pure vanilla extract: Enhances all the flavors with its deep, warming aroma.
- 2 eggs, at room temperature: Provide structure and moisture for soft, chewy cookies.
- 4 1/2 cups all-purpose flour: The sturdy base of the dough, giving your cookies shape and bite.
- 1 teaspoon baking soda: A little lift to make the cookies tender and soft.
- 1 teaspoon cinnamon: Classic fall spice that pairs perfectly with pumpkin shapes and chocolate.
- 1/2 teaspoon ginger: Adds a subtle warmth and complexity to the spice blend.
- 1/4 teaspoon nutmeg: Offers a rich, nutty touch that rounds out the flavor.
- 1/2 teaspoon salt: Balances the sweetness and enhances all the other flavors.
- 12 ounces milk chocolate, melted: The luscious filling that makes these cookies spectacularly gooey.
- 2 tablespoons salted butter: To brown gently and brush over the cookies for a nutty, toasted note.
- 3 tablespoons cinnamon sugar: Sprinkled on top for a sweet, crunchy finishing touch.
How to Make Milk Chocolate Stuffed Jack-O’-Lantern Cookies
Step 1: Cream the Butter and Sugar
Start by beating the softened butter, brown sugar, and vanilla extract together until the mixture becomes light and fluffy—this step is key for a tender, melt-in-your-mouth cookie base. Then, add eggs one at a time, blending thoroughly after each to maintain that perfect texture.
Step 2: Mix in Dry Ingredients to Form the Dough
Next, combine your flour with baking soda, cinnamon, ginger, nutmeg, and salt. Gradually add this dry mixture into your wet ingredients, beating just until combined and a soft dough ball forms. Overmixing here can lead to tough cookies, so keep it gentle and just bring everything together.
Step 3: Roll and Cut Out Pumpkin Shapes
Generously flour your work surface to prevent sticking, then split the dough into two discs. Roll each out to about a quarter inch thick. Use a pumpkin-shaped cookie cutter to create your cookie bases. For half the cookies, carefully carve out eyes and mouth shapes to create classic Jack-O’-Lantern faces—these will become the cookie tops.
Step 4: Chill and Bake
Place your cut cookies on parchment-lined baking sheets and freeze them until firm, about 15 to 20 minutes. This chilling step ensures they keep their shape while baking. When ready, bake at 350 degrees Fahrenheit for 8 to 12 minutes until just lightly golden. Allow them to cool slightly before moving them to a wire rack to cool completely.
Step 5: Brown Butter and Add Cinnamon Sugar
While the cookies cool, gently brown two tablespoons of butter in a medium pan until it smells toasted and nutty—this adds a beautiful depth of flavor. Brush this browned butter over the plain cookie halves, then sprinkle with cinnamon sugar for a delicate crunch and extra spice.
Step 6: Assemble Your Milk Chocolate Stuffed Jack-O’-Lantern Cookies
Finally, spread the melted milk chocolate onto the plain cookie halves, then top each with a Jack-O’-Lantern cookie face, pressing gently to sandwich the chocolate inside. These cookies can be enjoyed immediately for a warm, gooey treat or let the chocolate set for a few minutes for a firmer bite.
How to Serve Milk Chocolate Stuffed Jack-O’-Lantern Cookies
Garnishes
To elevate your Milk Chocolate Stuffed Jack-O’-Lantern Cookies, try dusting them with a light sprinkle of powdered sugar or drizzle with extra melted chocolate for a dazzling finish. Adding a few edible glitter specks or tiny candy eyes can also amp up the festive fun.
Side Dishes
These cookies pair beautifully with a warm cup of spiced apple cider or a creamy pumpkin latte—perfect companions that complement the cinnamon and ginger notes. For a heartier dessert spread, arrange alongside roasted nuts, fresh fruit like sliced pears, or a smooth vanilla bean ice cream.
Creative Ways to Present
Serve your Milk Chocolate Stuffed Jack-O’-Lantern Cookies on a rustic wooden board or festive Halloween platters scattered with autumn leaves and mini pumpkins. For a delightful party touch, tie each cookie sandwich with orange and black twine or place them in clear cellophane bags with seasonal tags for adorable take-home favors.
Make Ahead and Storage
Storing Leftovers
Keep your leftover Milk Chocolate Stuffed Jack-O’-Lantern Cookies fresh by placing them in an airtight container at room temperature. They’ll stay deliciously soft for up to three days, making them perfect for enjoying over several spooky evenings.
Freezing
You can freeze these cookies assembled or separately. Wrap tightly in plastic wrap and then place in a freezer-safe bag or container. When properly stored, they’ll keep for up to two months — ideal for baking ahead of the busy Halloween season.
Reheating
To warm them up, simply microwave the cookies on a plate for 10 to 15 seconds or until they’re just softened and the chocolate is melty. Avoid overheating to maintain their tender texture and gooey filling.
FAQs
Can I use dark chocolate instead of milk chocolate for the filling?
Absolutely! Dark chocolate will add a richer, slightly bittersweet contrast to the sweet and spiced cookies, making for a delicious variation on the classic Milk Chocolate Stuffed Jack-O’-Lantern Cookies.
How do I prevent the cookies from spreading too much during baking?
Chilling the dough and the cut cookies in the freezer before baking is essential. It helps the cookies keep their pumpkin shapes and Jack-O’-Lantern faces perfectly intact.
Can I make these cookies gluten-free?
Yes, by substituting the all-purpose flour with a gluten-free baking flour blend. Just make sure the blend includes xanthan gum or a similar binder to maintain the cookies’ texture and structure.
Is it possible to prepare the dough ahead of time?
Definitely! You can make the dough, shape the cookies, and freeze them on the baking sheets. When ready to bake, just pop them straight into the oven from the freezer—no need to thaw.
What’s the best way to melt the milk chocolate?
Use a gentle double boiler or microwave in short bursts, stirring frequently to prevent burning. Smooth, evenly melted chocolate will make spreading and assembling your Milk Chocolate Stuffed Jack-O’-Lantern Cookies a breeze.
Final Thoughts
I can’t recommend these Milk Chocolate Stuffed Jack-O’-Lantern Cookies enough—they’re a magical way to celebrate the flavors and fun of fall. With their festive design and irresistible combination of warm spices and creamy chocolate, they’re sure to become a beloved favorite in your seasonal baking repertoire. So gather your ingredients, roll up your sleeves, and get ready to fill your kitchen with the irresistible scent of fresh cookies and cozy autumn spices!
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Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe
- Total Time: 1 hour
- Yield: About 36 cookies 1x
- Diet: Vegetarian
Description
Delight in these festive Milk Chocolate Stuffed Jack-O’-Lantern Cookies, perfect for Halloween celebrations. Soft, spiced pumpkin-shaped cookies sandwich a rich milk chocolate filling, finished with a buttery cinnamon sugar topping for a sweet and cozy treat.
Ingredients
Cookie Dough
- 3 sticks (1 1/2 cups) salted butter, softened
- 1 1/4 cups light brown sugar, packed
- 1 tablespoon pure vanilla extract
- 2 eggs, at room temperature
- 4 1/2 cups all-purpose flour
- 1 teaspoon baking soda
- 1 teaspoon cinnamon
- 1/2 teaspoon ginger
- 1/4 teaspoon nutmeg
- 1/2 teaspoon salt
Filling and Topping
- 12 ounces milk chocolate, melted
- 2 tablespoons salted butter
- 3 tablespoons cinnamon sugar
Instructions
- Cream the Ingredients: In a large mixing bowl, cream together the softened butter, light brown sugar, and pure vanilla extract until the mixture is light and fluffy, which will take about 3 to 5 minutes. Add the eggs one at a time, mixing each until fully incorporated.
- Make the Dough: Add the all-purpose flour, baking soda, cinnamon, ginger, nutmeg, and salt to the creamed mixture. Beat until combined and the dough forms a ball. Generously flour your work surface to prevent sticking.
- Shape the Cookies: Divide the dough in half and flatten each half into a disk. Roll out each disk to approximately 1/4 inch thickness, using flour as needed to avoid sticking. Use a pumpkin-shaped cookie cutter to cut out cookies. Transfer cookies to a parchment-lined baking sheet. Using a paring knife or smaller cookie cutter, cut eyes and a mouth into half of the pumpkin cookies. Cover the baking sheet and freeze the cookies until firm, about 15-20 minutes. Roll out leftover scraps and repeat the process.
- Bake the Cookies: Preheat your oven to 350°F (175°C). Bake the cookies on the middle rack for 8 to 12 minutes until they are lightly golden around the edges but still soft in the center. Avoid overbaking. Cool cookies on the baking sheet for five minutes before transferring them to a wire rack to cool completely.
- Prepare the Topping: In a medium saucepan, add the 2 tablespoons of salted butter and melt over medium heat. Allow the butter to brown lightly until it smells toasted, about 2 to 3 minutes, stirring often. Remove from heat and let cool for 5 minutes. Brush the browned butter over the top of the cookies that do not have faces, then sprinkle with cinnamon sugar.
- Assemble the Cookies: Spread the melted milk chocolate over the flat half of the cookies without faces. Gently press the pumpkin-faced cookie halves on top of the chocolate-spread halves to form sandwiches. Serve immediately or allow the chocolate to firm up before storing in an airtight container for up to 3 days.
Notes
- Ensure the butter is at room temperature for easier creaming.
- Freezing the shaped cookies before baking helps preserve the details and prevents spreading.
- If you prefer a darker chocolate flavor, substitute milk chocolate with semi-sweet chocolate.
- Store the cookies in an airtight container at room temperature for up to 3 days for best freshness.
- You can prepare the dough a day ahead and refrigerate it tightly wrapped.
- Prep Time: 30 minutes
- Cook Time: 12 minutes
- Category: Dessert, Cookies
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 220 kcal
- Sugar: 15 g
- Sodium: 110 mg
- Fat: 12 g
- Saturated Fat: 7 g
- Unsaturated Fat: 4 g
- Trans Fat: 0.2 g
- Carbohydrates: 26 g
- Fiber: 1 g
- Protein: 3 g
- Cholesterol: 35 mg
Keywords: Halloween cookies, stuffed cookies, milk chocolate cookies, pumpkin cookies, spiced cookies, festive cookies
