Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe | Best for 2025

Looking for the perfect Halloween treat that’s both adorable and delicious? These Milk Chocolate Stuffed Jack-O’-Lantern Cookies are the answer! Soft, buttery sugar cookies shaped like cheerful jack-o’-lanterns, each hiding a delightful milk chocolate surprise, are guaranteed to be a crowd-pleaser.

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What are Milk Chocolate Stuffed Jack-O’-Lantern Cookies?

Ever wondered why some cookies have such whimsical names? Take these Milk Chocolate Stuffed Jack-O’-Lantern Cookies, for example. Are they haunted by a chocolate-loving ghost? Do they only come out at night during a full moon? Or perhaps, just maybe, they’re simply cookies shaped like pumpkins, filled with milk chocolate, and bursting with Halloween cheer!

We’ll leave the folklore to the storytellers, but we do know this: “the way to a man’s (or anyone’s!) heart is through his stomach,” and these cookies are a direct route. So, ditch the store-bought candy corn and bake up a batch of these bewitching beauties! We promise you won’t regret it!

Key Ingredients for Milk Chocolate Stuffed Jack-O’-Lantern Cookies:

Here’s a visual guide to all the ingredients you’ll need to conjour these delightful cookies:

  • All-Purpose Flour: 3 cups, plus more for dusting. Ensures the cookie dough has structure.
  • Baking Powder: 1 teaspoon. Helps the cookies rise and become light and airy.
  • Salt: 1/2 teaspoon. Balances the sweetness and enhances the flavors.
  • Unsalted Butter: 1 cup (2 sticks), softened. Provides richness and tenderness to the cookies. Make sure it’s properly softened, not melted, for the best texture.
  • Granulated Sugar: 1 cup. Adds sweetness and helps the cookies brown.
  • Large Eggs: 2. Binds the ingredients together and adds moisture.
  • Vanilla Extract: 1 teaspoon. Enhances the overall flavor of the cookies. Use pure vanilla extract for the best results.
  • Milk Chocolate: 12 ounces, chopped into small pieces or use milk chocolate chips. The delicious filling for our Jack-O’-Lanterns! Choose your favorite brand for the best flavor. Consider using individually wrapped chocolate candies which are conveniently portioned and easily stuffed.
  • Orange Gel Food Coloring: Adjust to achieve your desired shade of orange. Essential for giving the cookies their classic Jack-O’-Lantern color. Start with a few drops and gradually add more until you reach the desired intensity.
  • Black Gel Food Coloring: For decorating the faces on the jack-o’-lanterns. Provides a striking contrast against the orange cookies. A fine-tipped decorating nozzle helps create precise designs.
  • Powdered Sugar: 1/2 cup, for dusting. Adds a touch of sweetness and visual appeal.

How to Make Milk Chocolate Stuffed Jack-O’-Lantern Cookies:

Get ready to create a sweet Halloween masterpiece! These Milk Chocolate Stuffed Jack-O’-Lantern Cookies are surprisingly easy to make, and the result is incredibly rewarding. The soft, buttery cookie dough, combined with the creamy milk chocolate center, is a treat that will disappear faster than you can say “trick or treat!” All it takes is around 45 minutes of prep and bake time.

Step-by-Step Instructions:

  1. Prepare the Dough: In a medium bowl, whisk together the flour, baking powder, and salt.


  2. Cream the Butter and Sugar: In a large bowl, cream together the softened butter and granulated sugar until light and fluffy. This usually takes about 3-5 minutes with an electric mixer.


  3. Add Eggs and Vanilla: Beat in the eggs one at a time, then stir in the vanilla extract. Ensure each egg is fully incorporated before adding the next.


  4. Combine Wet and Dry Ingredients: Gradually add the dry ingredients to the wet ingredients, mixing until just combined. Be careful not to overmix, as this can result in tough cookies.


  5. Divide and Color the Dough: Divide the dough in half. Add orange gel food coloring to one half and mix until evenly colored. Wrap both halves of the dough in plastic wrap and chill in the refrigerator for at least 30 minutes. Chilling the dough will prevent it from spreading too much during baking.


  6. Preheat Oven and Prepare Baking Sheets: Preheat your oven to 375°F (190°C). Line baking sheets with parchment paper. Parchment paper will prevent the cookies from sticking and make cleanup easier.


  7. Roll and Cut the Dough: On a lightly floured surface, roll out the orange dough to about 1/4 inch thickness. Use a jack-o’-lantern cookie cutter (approximately 3 inches in size) to cut out shapes. Repeat with the plain dough. You should end up with an equal number of each.


  8. Stuff the Cookies: Place half of the orange cookies on the prepared baking sheets. Top each cookie with a generous amount of chopped milk chocolate.


  9. Top with the Second Cookie: Carefully place the plain cookies on top of the chocolate-covered cookies, gently pressing the edges to seal.


  10. Decorate with faces : Once cooled use black gel food coloring to add the eyes, nose and mouth.


  11. Bake the Cookies: Bake for 8-10 minutes, or until the edges are lightly golden brown. Be careful not to overbake, as the cookies will continue to bake slightly on the hot baking sheet.


  12. Cool and Serve: Let the cookies cool on the baking sheets for a few minutes before transferring them to a wire rack to cool completely. Dust with powdered sugar, if desired.


Why You’ll Love These Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Milk Chocolate Stuffed Jack-O'-Lantern Cookies
Milk Chocolate Stuffed Jack-O’-Lantern Cookies

The best part is undoubtedly the melty milk chocolate filling that oozes out with every bite! Forget store-bought cookies filled with preservatives and who-knows-what. These homemade treats are made with real butter, real chocolate, and real love! Not only are they more delicious, but they’re also much more cost-effective.

Plus, you can customize the level of sweetness and chocolate to your liking. Think about it a warm cookie with melted milk chocolate from the oven this Halloween.

If you’re a fan of classic sugar cookies or chocolate chip cookies, definitely give these filled delights a try, too!

What to Serve Milk Chocolate Stuffed Jack-O’-Lantern Cookies With:

  • A glass of cold milk: The classic pairing! The cool milk complements the warm, chocolatey cookies perfectly.
  • Hot chocolate: For an extra dose of comfort and warmth on a chilly Halloween evening.
  • Apple cider: A seasonally appropriate beverage that complements the flavors of fall.
  • Vanilla ice cream: Create a deliciously simple ice cream sandwich for an extra special treat.

Top Tips for Perfecting Milk Chocolate Stuffed Jack-O’-Lantern Cookies:

  • Use softened, not melted, butter: This is crucial for achieving a light and fluffy cookie dough.
  • Don’t overmix the dough: Overmixing develops the gluten in the flour, resulting in tough cookies. Mix until just combined.
  • Chill the dough: Chilling the dough prevents the cookies from spreading too much during baking.
  • Use a good quality milk chocolate: The better the chocolate, the better the cookies will taste.
  • Don’t overbake the cookies: Overbaked cookies will be dry and crumbly. Bake until the edges are lightly golden brown.
  • Substitute Butter for Vegan Butter: To Veganize this Recipe to cater for Vegan customers or friends.
  • Add Almond Essence : To achieve a warmer richer and more delicious flavour

Storing and Reheating Tips:

  • Storing: Store the completely cooled cookies in an airtight container at room temperature for up to 3-4 days.
  • Freezing Baked Cookies: Freeze baked cookies in a single layer on a baking sheet until solid. Transfer to a freezer-safe container or bag and store for up to 2-3 months. Thaw at room temperature before serving.
  • Freezing Dough: Freeze the dough balls before baking: Shape dough into balls, and freeze individually on a sheet for an hour, then transfer to freezer bag or container for 2-3 months. Thaw for an hour before baking!
  • Reheating: While these cookies are best enjoyed at room temperature, you can warm them slightly in the microwave for a few seconds if desired. Be careful not to overheat, as the chocolate filling will melt.

Final Thoughts:

These Milk Chocolate Stuffed Jack-O’-Lantern Cookies are a delightful way to celebrate Halloween! They’re fun to make, delicious to eat, and sure to bring a smile to everyone’s face. So, gather your ingredients, preheat your oven, and get ready to bake up some spooky good treats!

Discover more here : The Ultimate Baking Hub: Classic & Seasonal Recipes for Home Bakers

More Spooky & Delicious Recipes to Try:

FAQs

Can I use a different type of chocolate?

Absolutely! Milk chocolate is classic, but dark chocolate, semi-sweet chocolate, or even white chocolate would work well in this recipe. You can even use a combination of different chocolates for a more complex flavor.

Can I make these cookies ahead of time?

Yes, you can! You can prepare the dough ahead of time and store it in the refrigerator for up to 2 days, or in the freezer for up to 2 months. Just be sure to thaw the dough completely before rolling and cutting the cookies. Baked cookies can be made 1-2 days ahead of time.

Can I use a different cookie cutter shape?

Of course! While Jack-O’-Lanterns are perfect for Halloween, you can use any cookie cutter shape you like. Ghost, bat, or even simple circle shapes would work well.

The chocolate melted and leaked out while baking. What did I do wrong?

This can happen if the oven is too hot or if the edges of the cookies weren’t properly sealed. Make sure your oven is at the correct temperature and gently press the edges of the dough together to seal the chocolate filling inside.

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Milk Chocolate Stuffed Jack-O'-Lantern Cookies

Milk Chocolate Stuffed Jack-O’-Lantern Cookies


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5 from 1 review

  • Author: Ruthie Miller
  • Total Time: 40 minutes
  • Yield: 24 cookies 1x
  • Diet: Vegetarian

Description

Whimsical Halloween cookies shaped like pumpkins, filled with creamy milk chocolate, and decorated with jack-o’-lantern faces for a festive treat.


Ingredients

Scale
  • 3 cups all-purpose flour, plus more for dusting
  • 1 teaspoon baking powder
  • 1/2 teaspoon salt
  • 1 cup (2 sticks) unsalted butter, softened
  • 1 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 12 ounces milk chocolate, chopped or chips
  • Orange gel food coloring, as needed
  • Black gel food coloring, for decorating
  • 1/2 cup powdered sugar, for dusting

Instructions

  1. In a medium bowl, whisk together the flour, baking powder, and salt.
  2. In a large bowl, cream the butter and sugar until light and fluffy, about 3-5 minutes.
  3. Beat in the eggs one at a time, then add vanilla extract.
  4. Gradually add dry ingredients to wet ingredients, mixing until just combined.
  5. Divide dough in half. Color one half with orange gel food coloring. Wrap both in plastic wrap and chill at least 30 minutes.
  6. Preheat oven to 375°F (190°C). Line baking sheets with parchment paper.
  7. On a floured surface, roll out the orange dough to 1/4 inch thickness. Cut out pumpkin shapes with a jack-o’-lantern cookie cutter. Repeat with plain dough.
  8. Place half of the orange cookies on baking sheets and top each with chopped milk chocolate.
  9. Cover with a plain cookie and press edges gently to seal.
  10. Bake 8-10 minutes, until edges are lightly golden. Do not overbake.
  11. Cool on baking sheets for a few minutes, then transfer to a wire rack to cool completely.
  12. Once cooled, decorate with black gel food coloring for faces. Dust with powdered sugar if desired.

Notes

Use finely chopped chocolate or chocolate chips for easy stuffing. Ensure dough is well chilled to help cookies hold their shape.

  • Prep Time: 30 minutes
  • Cook Time: 10 minutes
  • Category: Dessert
  • Method: Baked
  • Cuisine: American

Nutrition

  • Serving Size: 1 cookie
  • Calories: 180
  • Sugar: 14g
  • Sodium: 85mg
  • Fat: 9g
  • Saturated Fat: 5g
  • Unsaturated Fat: 3g
  • Trans Fat: 0g
  • Carbohydrates: 22g
  • Fiber: 1g
  • Protein: 2g
  • Cholesterol: 25mg

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