If you’re ready for a treat that brings together festive fun and pure chocolatey bliss, these Milk Chocolate Stuffed Jack-O’-Lantern Cookies are about to become your new seasonal favorite. Picture this: buttery, spiced sugar cookies, glowing orange and shaped like cheery pumpkins, each one hiding a secret center of melty milk chocolate. Whether you’re baking for a Halloween bash, a cozy fall afternoon, or just because you can’t resist that adorable jack-o’-lantern grin, these cookies are sure to delight kids and adults alike. Get ready to fall in love with every soft, gooey bite of these irresistibly charming Milk Chocolate Stuffed Jack-O’-Lantern Cookies.
Ingredients You’ll Need
Each ingredient in this recipe plays a starring role, building the irresistible flavor, vibrant color, and melt-in-your-mouth texture of these cookies. Don’t worry—they’re all pantry staples, but together they create pure magic.
- All-purpose flour: The foundation of our cookie, providing structure and that classic tender crumb.
- Baking powder: A touch of lift keeps the cookies soft and just the right amount of fluffy.
- Salt: Balances sweetness and makes every flavor pop.
- Ground cinnamon: Adds cozy warmth and subtle spice that says “autumn.”
- Unsalted butter (softened): For rich flavor and a perfectly soft, melt-in-your-mouth texture.
- Granulated sugar: Creates sweetness and helps the cookies hold their shape.
- Light brown sugar (packed): Adds moisture and a gentle caramel note for extra depth.
- Large egg: Binds everything together and gives the dough a little lift.
- Vanilla extract: Brings warmth and rounds out the cookie’s flavors.
- Orange food coloring (optional): Gives your cookies that classic pumpkin hue—totally fun, but optional.
- Milk chocolate (cut into squares or pieces): The secret surprise inside—choose your favorite creamy milk chocolate for a gooey center.
- Milk (if needed): Just a splash to help bring your dough together if it feels a little dry.
How to Make Milk Chocolate Stuffed Jack-O’-Lantern Cookies
Step 1: Mix the Dry Ingredients
Start by whisking together the flour, baking powder, salt, and cinnamon in a medium bowl. This ensures all your dry ingredients are evenly distributed, so every bite of your Milk Chocolate Stuffed Jack-O’-Lantern Cookies is perfectly spiced and fluffy.
Step 2: Cream the Butter and Sugars
In a large mixing bowl, beat the softened butter, granulated sugar, and brown sugar until the mixture is light and fluffy. This step is key for that melt-in-your-mouth texture. Take your time—it’s worth it for cookies that taste like pure bakery magic.
Step 3: Add the Egg, Vanilla, and Color
Beat in the egg and vanilla extract until just combined. If you want your cookies to have that true pumpkin glow, stir in the orange food coloring now. It’s totally optional, but it makes the jack-o’-lantern faces pop!
Step 4: Combine Wet and Dry Mixtures
Gradually add your dry ingredients to the creamed mixture, stirring until a soft dough forms. If your dough feels a bit dry or crumbly, add a tablespoon of milk to bring it all together. The dough should be soft, but not sticky.
Step 5: Roll and Cut the Dough
Divide the dough in half and roll each portion out on a floured surface to about 1/4-inch thickness. Use a pumpkin-shaped cookie cutter to cut out an even number of cookies—these will be the tops and bottoms of your Milk Chocolate Stuffed Jack-O’-Lantern Cookies.
Step 6: Carve the Jack-O’-Lantern Faces
On half of your cookie cut-outs, use a small sharp knife or paring tool to carefully carve little jack-o’-lantern faces. This is the step where you can get creative—classic grins, spooky smiles, or whatever expression makes you happy!
Step 7: Fill and Assemble
Place a piece of milk chocolate on each whole (uncut) cookie. Gently top with a jack-o’-lantern face cookie, and press the edges together to seal in that chocolatey goodness. Make sure the edges are well sealed so the chocolate doesn’t escape during baking.
Step 8: Chill the Cookies
Transfer your assembled cookies to a baking sheet and chill them in the refrigerator for about 20 minutes. This helps the cookies hold their shape and keeps the faces looking sharp when they bake.
Step 9: Bake to Perfection
Preheat your oven to 350°F and line your baking sheets with parchment paper. Bake the cookies for 10–12 minutes, just until the edges are lightly golden. Let them cool on the pan for 5 minutes, then transfer to a wire rack. Enjoy them warm for gooey centers or let them cool for neatly filled cookies.
How to Serve Milk Chocolate Stuffed Jack-O’-Lantern Cookies
Garnishes
For an extra festive touch, dust your cookies lightly with powdered sugar or add a drizzle of melted chocolate across the tops. Edible glitter or orange sanding sugar will make them sparkle, perfect for party platters or special occasions.
Side Dishes
These cookies pair beautifully with a mug of hot cocoa, spiced apple cider, or a scoop of vanilla ice cream. For a snack spread, serve them with fresh fruit or a platter of mixed nuts to balance the sweetness.
Creative Ways to Present
Stack your Milk Chocolate Stuffed Jack-O’-Lantern Cookies on a rustic wooden board for a Halloween party centerpiece, or wrap them in cellophane bags tied with orange ribbon for festive gifts. You can even use them as edible place cards by piping names in chocolate beneath each jack-o’-lantern face!
Make Ahead and Storage
Storing Leftovers
If you have any cookies left (lucky you!), store them in an airtight container at room temperature for up to 4 days. They’ll stay soft, and the chocolate center will remain wonderfully creamy.
Freezing
These cookies freeze like a dream! Freeze unbaked, assembled cookies on a tray, then transfer to a zip-top bag for up to 2 months. You can also freeze baked cookies and thaw at room temperature—just note the faces may lose a bit of crispness.
Reheating
To get that gooey milk chocolate center back, warm the cookies in a 300°F oven for 2–3 minutes. Or give them a quick zap in the microwave for about 10 seconds—just enough for the chocolate to melt without overheating the cookie.
FAQs
Can I substitute the milk chocolate with something else?
Absolutely! You can swap in dark chocolate, white chocolate, Nutella, or even pieces of peanut butter cups for a fun twist. Just be sure to use the same amount so the cookies seal well.
What if I don’t have a pumpkin-shaped cookie cutter?
No worries—use a round biscuit cutter or even a drinking glass, then carve pumpkin lines and faces by hand. They’ll still look adorable and taste just as delicious.
How do I keep the cookies from spreading too much?
Chilling the assembled cookies before baking is key. It helps the dough hold its shape so those jack-o’-lantern faces stay sharp and defined in your Milk Chocolate Stuffed Jack-O’-Lantern Cookies.
Can I make the dough ahead of time?
Yes! Make the dough up to two days in advance and store it tightly wrapped in the fridge. You can also freeze the dough for a month—just thaw overnight in the fridge before rolling and cutting.
Do I need to use orange food coloring?
Not at all! The coloring is purely for fun and presentation. If you skip it, your cookies will still taste amazing—they just won’t have that classic pumpkin hue.
Final Thoughts
There’s nothing quite like the playful spirit and cozy flavors of Milk Chocolate Stuffed Jack-O’-Lantern Cookies. Whether you’re baking them for a spooky celebration or just to bring a little extra joy to your fall, these cookies are sure to bring out smiles and spark a little magic in your kitchen. Give them a try—you might just find a new tradition!
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Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe
- Total Time: 37 minutes (plus 20 minutes chilling)
- Yield: 16 sandwich cookies 1x
- Diet: Vegetarian
Description
Delight in these festive Milk Chocolate Stuffed Jack-O’-Lantern Cookies, perfect for Halloween celebrations. Soft, cinnamon-spiced cookie dough encases a creamy milk chocolate center, creating a gooey surprise with every bite. These charming pumpkin-shaped sandwich cookies combine classic fall flavors with a fun twist, ideal for parties or seasonal treats.
Ingredients
Dry Ingredients
- 2 1/2 cups all-purpose flour
- 1/2 teaspoon baking powder
- 1/2 teaspoon salt
- 1/2 teaspoon ground cinnamon
Wet Ingredients
- 1 cup unsalted butter, softened
- 3/4 cup granulated sugar
- 1/2 cup light brown sugar, packed
- 1 large egg
- 1 teaspoon vanilla extract
- 1/2 teaspoon orange food coloring (optional)
- 1 tablespoon milk (if needed for dough consistency)
Filling
- 4 ounces milk chocolate, cut into squares or pieces
Instructions
- Mix Dry Ingredients: In a medium bowl, whisk together the all-purpose flour, baking powder, salt, and ground cinnamon to ensure even distribution of leavening and spices.
- Cream Butter and Sugars: In a large bowl, beat the softened unsalted butter with granulated and light brown sugars until the mixture is light and fluffy, which helps incorporate air for a tender cookie.
- Add Egg and Flavorings: Beat in the large egg and vanilla extract until fully combined. Stir in orange food coloring if you’d like to give the cookies a festive pumpkin hue.
- Combine Wet and Dry Ingredients: Gradually add the dry ingredients to the wet mixture, blending until a soft dough forms. If the dough feels dry, add 1 tablespoon of milk to achieve the right consistency.
- Roll and Cut Dough: Divide the dough into two equal parts. Roll each half out on a floured surface to about 1/4-inch thickness. Use a pumpkin-shaped cookie cutter to cut out an even number of cookies. On half of them, carefully cut out jack-o’-lantern faces using a small knife or paring tool.
- Assemble Cookies: Place a piece of milk chocolate in the center of each whole cookie. Top with a cut-out jack-o’-lantern face cookie and gently press the edges together, sealing the chocolate inside to create stuffed sandwich cookies.
- Chill: Put the assembled cookies in the refrigerator for 20 minutes to help them set, which prevents spreading during baking.
- Preheat and Prepare: Preheat your oven to 350°F (175°C). Line baking sheets with parchment paper for easy cleanup and to prevent sticking.
- Bake: Bake the chilled cookies for 10–12 minutes, or until the edges turn just golden. Remove from oven and let cool on the baking sheets for 5 minutes.
- Cool and Serve: Transfer the cookies to a wire rack to cool completely. Enjoy them warm for gooey chocolate centers or cooled for a firmer texture.
Notes
- Substitute milk chocolate with dark chocolate, Nutella, or peanut butter cups for different filling flavors.
- Add pumpkin pie spice to the dough to enhance the seasonal flavor profile.
- Cookies freeze well both before and after baking, making them perfect for advance preparation.
- Prep Time: 25 minutes
- Cook Time: 12 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 sandwich cookie
- Calories: 260
- Sugar: 17g
- Sodium: 105mg
- Fat: 14g
- Saturated Fat: 8g
- Unsaturated Fat: 5g
- Trans Fat: 0g
- Carbohydrates: 30g
- Fiber: 1g
- Protein: 2g
- Cholesterol: 35mg
