Name: Milk Chocolate Stuffed Jack-O'-Lantern Cookies
Prep time: 20 min
Cook time: 12 min
Total time: 32 min
Cuisine: American
Ingredients: 1 1/2 cups salted butter; 1 1/4 cups light brown sugar; 2 eggs; 4 1/2 cups all-purpose flour; 12 ounces milk chocolate; Cinnamon sugar for topping

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If you’re looking for a delightful treat that brings smiles to faces and warmth to hearts, you’ve landed in the right place! These Milk Chocolate Stuffed Jack-O’-Lantern Cookies are a family favorite in my house. The combination of spiced brown sugar cookies and gooey milk chocolate creates a sweet surprise that’s simply irresistible.

Perfect for Halloween gatherings or cozy Thanksgiving dinners, these cookies are sure to become a cherished recipe. Plus, they’re great for busy weeknights when you just need something comforting and delicious.

Why You’ll Love This Recipe

Easy to make: With simple steps and straightforward ingredients, baking these cookies is a breeze!
Family-friendly: Kids love helping out in the kitchen, especially when it involves cookie cutting and chocolate!
Perfect for sharing: Whether it’s a Halloween party or a neighborly gift, these cookies are an instant hit.
Make ahead option: You can prepare the dough in advance and bake fresh cookies whenever the craving hits.
Delicious flavor: The warm spices combined with rich milk chocolate make every bite a little piece of heaven.

Ingredients You’ll Need

Gathering your ingredients is part of the fun! You will find that these are simple, wholesome ingredients that come together beautifully. Let’s dive into what you’ll need to whip up these delightful cookies:

For the 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

For the Filling and Topping

12 ounces milk chocolate, melted
2 tablespoons salted butter
3 tablespoons cinnamon sugar

Variations

One of the best parts about this recipe is its flexibility! Feel free to get creative with your cookie fillings or decorations. Here are some fun ideas:

Change up the chocolate: Use dark chocolate or white chocolate if that’s more your style!
Add nuts: Chopped pecans or walnuts can add a lovely crunch to the filling.
Spice it up: Experiment by adding different spices like cardamom or allspice for unique flavors.
Decorate differently: Try frosting instead of cinnamon sugar for a colorful twist!

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

Step 1: Cream the Butter and Sugar

In a large mixing bowl, cream together the softened butter, packed brown sugar, and pure vanilla extract until light and fluffy—about 3-5 minutes. This step is vital as it helps incorporate air into the mixture, giving your cookies that lovely soft texture. Once fluffy, add the eggs one at a time, mixing well after each addition.

Step 2: Combine Dry Ingredients

Now it’s time to add in your dry ingredients—4 1/2 cups of all-purpose flour, 1 teaspoon baking soda, 1 teaspoon cinnamon, 1/2 teaspoon ginger, 1/4 teaspoon nutmeg, and 1/2 teaspoon salt. Mix until everything is just combined; don’t overwork the dough! It should come together nicely into a ball.

Step 3: Roll Out the Dough

Flour your work surface generously! Divide your dough in half and flatten each half into a disk. Roll out each disk to about 1/4 inch thickness. Using a pumpkin cookie cutter, cut out your cookies. Carefully transfer them onto a parchment-lined baking sheet. Don’t forget to cut out eyes and mouths on half of them with either a pairing knife or another small cookie cutter!

Step 4: Chill Before Baking

Cover your baking sheet with cut-out cookies and pop them into the freezer for about 15-20 minutes. Chilling helps prevent spreading while baking so you’ll have those cute pumpkin shapes intact.

Step 5: Bake Your Cookies

Preheat your oven to 350 degrees Fahrenheit. Bake your pumpkin-shaped cookies on the middle rack for about 8-12 minutes until they’re just lightly golden brown. Keep an eye on them; we want soft cookies here! After baking, cool them on the sheet for about five minutes before transferring them to a wire rack.

Step 6: Add Cinnamon Sugar Topping

In a medium pot over low heat, melt down some butter until it slightly browns—this adds such depth of flavor! Remove from heat after about 2-3 minutes and let cool for five minutes. Brush this deliciously toasted butter over the top half of your cookies and sprinkle with cinnamon sugar for that perfect finishing touch.

Step 7: Assemble Your Cookies

Time for the fun part! Spread melted milk chocolate over half of your cookie bottoms (the ones without faces). Place the top pumpkin-faced cookies gently over these chocolatey halves and press them down slightly so they stick together. You can serve these right away or let them sit so that chocolate firms up before storing in an airtight container for up to three days.

With each bite of these Milk Chocolate Stuffed Jack-O’-Lantern Cookies, you’ll be reminded of cozy gatherings filled with laughter and joy. Happy baking!

Pro Tips for Making Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Baking can be a delightful adventure, and with a few handy tips, you can ensure your cookies turn out perfectly every time!

Use room temperature ingredients: Starting with butter and eggs that are at room temperature helps to create a smoother dough that mixes more evenly, resulting in a better texture.
Don’t skip the chilling step: Freezing the cut-out cookies before baking prevents them from spreading too much in the oven. This ensures they maintain their adorable pumpkin shape!
Watch your baking time closely: Ovens can vary, so keep an eye on your cookies as they bake. Remove them when they’re just lightly golden to ensure they stay soft and chewy.
Experiment with chocolate types: While milk chocolate is delicious, try swapping in dark or semi-sweet chocolate for a richer flavor profile. This adds a fun twist to the classic recipe!
Store properly: To keep your cookies fresh, store them in an airtight container. If you prefer a softer cookie, add a slice of bread to the container; it helps retain moisture.

How to Serve Milk Chocolate Stuffed Jack-O’-Lantern Cookies

These delightful cookies are perfect for any festive occasion! With some clever presentation ideas, you can impress your guests whether it’s Halloween or Thanksgiving.

Garnishes

Whipped cream: A dollop of freshly whipped cream on the side adds a wonderful richness that complements the sweet chocolate filling.
Chocolate drizzle: A light drizzle of melted chocolate over the top of the cookies creates an elegant touch and enhances their appearance.

Side Dishes

Pumpkin spice hot chocolate: A warm cup of pumpkin spice hot chocolate pairs beautifully with these cookies and creates a cozy atmosphere.
Apple cider: Serve chilled or warmed apple cider as a refreshing complement to the rich flavors of the cookies.
Caramel popcorn: The sweet crunch of caramel corn can provide a delightful contrast to the soft cookies and makes for an exciting snack mix.
Vanilla ice cream: A scoop of creamy vanilla ice cream alongside these cookies offers a delicious combination that elevates dessert time!

Enjoy making, sharing, and savoring these Milk Chocolate Stuffed Jack-O’-Lantern Cookies with family and friends! Happy baking!

Make Ahead and Storage

These Milk Chocolate Stuffed Jack-O’-Lantern Cookies are perfect for meal prep, whether you’re planning a Halloween party or simply want to enjoy a sweet treat throughout the week. Here’s how to keep your cookies fresh and ready to enjoy!

Storing Leftovers

Store cookies in an airtight container at room temperature.
They will stay fresh for up to 3 days.
If you want to keep them longer, consider freezing them.

Freezing

Let the cookies cool completely before freezing.
Place them in a single layer on a baking sheet and freeze until solid.
Transfer frozen cookies to an airtight container or freezer bag, separating layers with parchment paper.
They can be stored in the freezer for up to 3 months.

Reheating

For best results, reheat cookies in the oven at 350°F for about 5-7 minutes.
You can also microwave them for about 10-15 seconds, but this may make them softer.

FAQs

Here are some common questions about these delightful cookies:

Can I make Milk Chocolate Stuffed Jack-O’-Lantern Cookies without eggs?

Yes! You can substitute each egg with a flaxseed meal (1 tablespoon flaxseed meal + 2.5 tablespoons water per egg). Let it sit for a few minutes until it thickens.

What kind of chocolate should I use for the Milk Chocolate Stuffed Jack-O’-Lantern Cookies?

Feel free to use any type of milk chocolate that you prefer, whether it’s chocolate chips or a chocolate bar that you melt down yourself.

How can I decorate my Milk Chocolate Stuffed Jack-O’-Lantern Cookies?

You can use icing or edible markers to add more details to your jack-o’-lantern faces after baking! Get creative with different expressions!

Can I use different spices in my Milk Chocolate Stuffed Jack-O’-Lantern Cookies?

Absolutely! If you prefer other spices like allspice or cloves, feel free to substitute according to your taste preferences.

Final Thoughts

I hope you enjoy making these Milk Chocolate Stuffed Jack-O’-Lantern Cookies as much as I do! They’re not only delicious but also bring a festive touch to any gathering. Whether you’re sharing them with friends or enjoying them solo with a cup of tea, these cookies are sure to warm your heart. Happy baking!

Milk Chocolate Stuffed Jack-O’-Lantern Cookies

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Author: Amelia
Prep Time: 20 minutes
Cook Time: 12 minutes
Total Time: 32 minutes
Yield: Approximately 24 cookies 1x
Category: Dessert
Method: Baking
Cuisine: American

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Description

If you’re searching for a delightful dessert to brighten up your gatherings, look no further than Milk Chocolate Stuffed Jack-O’-Lantern Cookies! These charming cookies are crafted with spiced brown sugar dough and filled with luscious milk chocolate, making each bite a sweet surprise. Perfect for Halloween festivities or cozy autumn evenings, these cookies are not only fun to make but also a treat that family and friends will adore. With easy preparation steps and the option to customize fillings, these cookies are sure to become a beloved addition to your recipe collection.

Ingredients

Scale

1 1/2 cups salted butter
1 1/4 cups light brown sugar
2 eggs
4 1/2 cups all-purpose flour
12 ounces milk chocolate
Cinnamon sugar for topping

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Instructions

Cream softened butter and brown sugar until fluffy. Add eggs one at a time.
Mix in flour, baking soda, cinnamon, ginger, nutmeg, and salt until combined.
Roll out dough and cut into pumpkin shapes, cutting out faces on half.
Chill cookies in the freezer for 15-20 minutes.
Bake at 350°F for 8-12 minutes until lightly golden. Cool on wire rack.
Brush melted butter on top half and sprinkle with cinnamon sugar.
Assemble by spreading melted chocolate on the cookie bottoms and pressing together.