If you’re searching for a truly festive treat that’s as fun to make as it is to eat, look no further than Milk Chocolate Stuffed Jack-O’-Lantern Cookies! These adorable pumpkin-shaped cookies are bursting with creamy milk chocolate centers and feature charming jack-o’-lantern faces just perfect for fall gatherings or a special Halloween night. With every buttery, orange-tinted bite, you’ll fall in love with their melt-in-your-mouth texture, playful appearance, and surprise chocolate filling—a magical upgrade on classic sandwich cookies. Get ready to delight kids and grown-ups alike with this unforgettable homemade delight!
Ingredients You’ll Need
For these Milk Chocolate Stuffed Jack-O’-Lantern Cookies, the ingredient list may look simple, but every component plays a starring role. From the rich, golden butter to the vibrant orange food coloring and silky-smooth milk chocolate, each item helps achieve the cookie’s signature taste, color, and festive charm.
- All-purpose flour: This forms the backbone of your cookies, giving them structure and the perfect crisp-tender bite.
- Baking powder: Just a touch helps the cookies puff up ever so slightly, ensuring they’re tender instead of dense.
- Salt: Enhances flavor by balancing the sweetness and bringing out the richness of the chocolate and butter.
- Unsalted butter (softened): Essential for that melt-in-your-mouth, buttery crumb; make sure it’s room temperature for easy blending.
- Granulated sugar: Sweetens the dough and gives the cookies a lightness that pairs perfectly with the milk chocolate filling.
- Large egg: Binds your dough and adds just enough richness for a soft cookie texture.
- Vanilla extract: Brings warmth and a comforting aroma that’s hard to resist in any homemade cookie.
- Orange food coloring (or red & yellow mix): Turns your cookies a festive, pumpkin-inspired hue—use gel coloring for the brightest results.
- Milk chocolate bars (broken into squares): The star of the filling—choose a creamy, good-quality milk chocolate for gooey, decadent centers.
- Milk (if needed for melting chocolate): Helps achieve a luscious melted chocolate texture if you want to soften the squares further.
How to Make Milk Chocolate Stuffed Jack-O’-Lantern Cookies
Step 1: Mix the Dry Ingredients
Start by whisking together the flour, baking powder, and salt in a medium bowl. This step is crucial for even distribution, so your cookies bake up with perfectly balanced flavor and just the right amount of lift.
Step 2: Cream the Butter and Sugar
In a large mixing bowl, use an electric mixer to beat together your softened butter and granulated sugar. Give it a good 2 to 3 minutes—your mixture should look light, fluffy, and creamy, which means air is getting incorporated for that irresistible texture.
Step 3: Add Wet Ingredients and Color
Beat in the egg, vanilla extract, and orange food coloring (or your custom red-and-yellow blend). Don’t hold back with the coloring—the more vibrant, the more striking your jack-o’-lanterns will be.
Step 4: Combine Wet and Dry Mixtures
Gradually add your dry ingredients into the butter mixture, mixing until a soft, slightly sticky dough forms. Over-mixing can make your cookies tough, so go just until the flour disappears.
Step 5: Chill the Dough
Divide the dough in half, flatten each into a disc, wrap in plastic, and refrigerate for 1 hour. This makes the dough easier to handle and helps your cookies keep their perfect pumpkin shape while baking.
Step 6: Roll and Cut the Cookies
On a lightly floured surface, roll one dough disc out to about 1/4-inch thickness. Use a pumpkin-shaped cookie cutter to cut out pairs of cookies, then, for half of them, use a small knife to create jack-o’-lantern faces—it’s your chance to get creative!
Step 7: Assemble the Cookies
Arrange the solid cookies on lined baking sheets, top each with a square of milk chocolate, then gently press a “face” cookie on top. Seal the edges by pressing gently—this way the molten chocolate stays tucked away inside.
Step 8: Bake to Perfection
Bake at 350°F (175°C) for 10 to 12 minutes, or until the edges are set but not browned. Allow the cookies to cool on the baking sheet for 5 minutes before transferring to a wire rack—this helps them firm up so you can enjoy that signature milk chocolate-stuffed center.
How to Serve Milk Chocolate Stuffed Jack-O’-Lantern Cookies
Garnishes
While these cookies are utterly charming on their own, a quick dusting of powdered sugar or a few drizzles of melted chocolate can add extra flair. For a festive sparkle, try edible glitter or tiny candies tucked into the jack-o’-lantern eyes and mouths!
Side Dishes
Pair these Milk Chocolate Stuffed Jack-O’-Lantern Cookies with icy glasses of milk, mugs of warm apple cider, or—for a grown-up twist—a rich hot chocolate. Their sweet, chocolaty richness contrasts deliciously with tart fruit or even a scoop of vanilla ice cream.
Creative Ways to Present
For a show-stopping Halloween dessert table, pile the cookies onto a rustic wooden board surrounded by mini pumpkins and fall leaves. Or, tuck them into cellophane bags tied with orange ribbon as a memorable party favor. Their playful faces just beg to be the centerpiece of your autumn celebrations!
Make Ahead and Storage
Storing Leftovers
Keep any extra Milk Chocolate Stuffed Jack-O’-Lantern Cookies fresh by storing them in an airtight container at room temperature. They’ll stay perfectly soft and flavorful for up to three days, making them great for lunchboxes or on-the-go snacks.
Freezing
If you want to enjoy these cookies well after pumpkin season, freeze them! Wrap cooled cookies individually in plastic wrap, then transfer to a freezer-safe bag. They’ll hold up beautifully for up to two months—just thaw at room temperature when you’re ready to indulge.
Reheating
For that magical, gooey chocolate center, pop a cookie in the microwave for about 10 seconds. This reawakens the milk chocolate filling and brings you right back to freshly baked bliss, even days later.
FAQs
Can I use a different type Dessert
Absolutely! Dark or white chocolate both make fabulous substitutions for the milk chocolate if you want to mix things up or cater to different tastes.
Do I have to chill the dough?
Chilling is key—it not only makes rolling and cutting easier, but also ensures the cookies hold their shape and have that perfect, tender bite when baked.
My jack-o’-lantern faces are spreading. Any tips?
If the dough gets too warm, the cookies can spread. Make sure your baking sheets are cool and pop the assembled cookies into the fridge for a few minutes before baking to help them keep crisp details.
Can I make the dough ahead of time?
Yes! You can make the dough up to two days ahead, wrap it tightly in plastic wrap, and keep it chilled until you’re ready to roll, cut, and bake.
Are these cookies safe for kids with nut allergies?
The recipe itself is nut-free, but always double-check your chocolate bars and other ingredients for cross-contamination warnings, especially if you’re serving these to children with allergies.
Final Thoughts
There’s something irresistible about the combination of playful design, buttery cookie, and silky melted chocolate in these Milk Chocolate Stuffed Jack-O’-Lantern Cookies. Whether you’re baking for a crowd or just to brighten your own autumn day, make a batch and experience for yourself why these cookies have quickly become a must-have on my fall baking list. Go ahead and give them a try—your kitchen (and your friends) will thank you!
Print
Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe
- Prep Time: 20 minutes plus chilling
- Cook Time: 12 minutes
- Total Time: 1 hour 15 minutes
- Yield: 20 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Description
These Milk Chocolate Stuffed Jack-O’-Lantern Cookies are perfect for Halloween with a surprise chocolate center inside a delicious sugar cookie. Fun to make and even more fun to eat!
Ingredients
Dough:
- 2 1/2 cups all-purpose flour
- 1/2 teaspoon baking powder
- 1/4 teaspoon salt
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 1/2 teaspoon orange food coloring (or a mix of red and yellow)
Filling:
- 8 ounces milk chocolate bars, broken into squares
- 1 tablespoon milk (if needed for melting chocolate)
Instructions
- Prepare Dough: In a medium bowl, whisk together flour, baking powder, and salt. In a large mixing bowl, beat butter and sugar until light and fluffy. Add egg, vanilla, and food coloring, mix well. Gradually add dry ingredients, mix into a soft dough. Chill dough for 1 hour.
- Shape and Fill: Roll out dough, cut out pumpkin-shaped cookies. Cut faces in half of the cookies. Place chocolate square on solid cookies, top with face cookie, seal edges.
- Bake: Bake at 350°F (175°C) for 10–12 minutes. Cool on sheet before transferring to wire rack.
- Serve: Enjoy warm for a melty center or at room temperature for firmer cookies.
Notes
- You can swap milk chocolate with dark or white chocolate for variety.
- Add 1 teaspoon of pumpkin pie spice to the dough for a fall twist.
- Store cookies in an airtight container for up to 3 days.
Nutrition
- Serving Size: 1 cookie
- Calories: 190
- Sugar: 15 g
- Sodium: 70 mg
- Fat: 10 g
- Saturated Fat: 6 g
- Unsaturated Fat: 4 g
- Trans Fat: 0 g
- Carbohydrates: 25 g
- Fiber: 1 g
- Protein: 2 g
- Cholesterol: 25 mg
