Jack-o’-Lantern Chocolate Sugar Cookies

October has a magical way of transforming everyday treats into spooky delights, and these Jack-o’-Lantern Chocolate Sugar Cookies are a prime example. Last year, my kids and I had a blast making these for our Halloween party, and they were the first treats to disappear! Get ready to bring some Halloween magic into your kitchen, one adorable cookie at a time.

These cookies combine my go-to chocolate sugar cookie recipe with a creamy, tangy cream cheese frosting. The pumpkin shapes and jack-o’-lantern faces add a touch of whimsy, making them perfect for all ages. Plus, the process is surprisingly simple, even if you’re a beginner baker.

Why You’ll Love It

These Jack-o’-Lantern Chocolate Sugar Cookies aren’t just cute; they’re packed with deliciousness. The rich chocolate cookies combined with the creamy, tangy orange frosting create a perfect balance of flavors. They’re easy to make and are guaranteed to bring a smile to everyone’s face. Plus, they’re perfect for sharing, whether you’re hosting a Halloween party or gifting them to friends and family.

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Ingredient Lowdown

Here’s what you’ll need to make these spooky-sweet treats. I’ve included some helpful notes on key ingredients.

For the chocolate sugar cookies:

• 2 1/2 cups (318 grams) all-purpose flour
• 1/2 cup (50 grams) Dutch-process cocoa powder (for rich color and flavor, but natural unsweetened works too!)
• 1 teaspoon baking powder
• 1/4 teaspoon fine sea salt
• 1 1/2 sticks (170 grams) unsalted butter, softened
• 1 cup (200 grams) granulated sugar
• 2 large eggs, at room temperature
• 1 teaspoon pure vanilla extract

For the cream cheese frosting:

• 4 ounces (113 grams) cream cheese, softened
• 4 tablespoons (57 grams) unsalted butter, softened
• 2 teaspoons vanilla extract
• 1 1/2 cups (188 grams) powdered sugar, sifted (sifting prevents lumps!)
• A few drops of orange gel food coloring

From Start to Finish

Step 1: Make the Chocolate Sugar Cookies

In a medium bowl, whisk together the flour, cocoa powder, baking powder, and salt. In a separate large bowl, cream together the softened butter and sugar until light and fluffy. Beat in the eggs one at a time, then stir in the vanilla extract. Gradually add the dry ingredients to the wet ingredients, mixing until just combined. Don’t overmix!

Step 2: Roll and Chill

Divide the dough in half, flatten each half into a disk, and wrap in plastic wrap. Chill for at least 1 hour (or up to 3 days).

Step 3: Cut Out the Cookies

Preheat your oven to 350°F (175°C). On a lightly floured surface, roll out the chilled dough to about 1/4-inch thickness. Use a pumpkin-shaped cookie cutter to cut out the cookies. Using a smaller cookie cutter or knife, cut out triangle eyes and a mouth in half of the pumpkin shapes to create the jack-o’-lantern faces. Place the cookies on baking sheets lined with parchment paper.

Step 4: Bake

Bake for 8-10 minutes, or until the edges are set. Let the cookies cool on the baking sheets for a few minutes before transferring them to a wire rack to cool completely.

Step 5: Make the Cream Cheese Frosting

While the cookies are cooling, beat the softened cream cheese and butter together until smooth. Add the vanilla extract and gradually beat in the sifted powdered sugar. Mix until light and fluffy. Add a few drops of orange food coloring and mix until desired color is reached.

Step 6: Assemble the Cookies

Once the cookies are completely cool, frost the bottom sides of the plain pumpkin cookies with the cream cheese frosting. Top with the jack-o’-lantern face cookies, pressing gently to create a sandwich.

Better-Than-Grandma Tips

• Chill out: Chilling the dough is crucial for preventing spreading. Trust me, nobody wants flat jack-o’-lanterns! Chilling also helps the cutouts hold their shape.
• Soft touch: When rerolling scraps, be gentle. Overworking the dough can make your cookies tough.
• Even baking: Make sure your oven is properly preheated and use a reliable oven thermometer for consistent results. Sometimes ovens can run a little hot or cold, which affects baking. Check out our guide on oven temperature calibration for more details.
• Frosting fun: For a vibrant orange hue, use gel food coloring. A little goes a long way!

Try These Variations

• Spice it up: Add a teaspoon of pumpkin pie spice or cinnamon to the cookie dough for a warm, autumnal flavor.
• Chocolate lovers: Dip the frosted cookies in melted dark chocolate for an extra decadent treat. You can find my favorite chocolate dipping techniques in my Chocolate Covered Strawberries post.
• Festive sprinkles: Decorate the frosted cookies with Halloween-themed sprinkles for extra flair.
• Different faces: Use a variety of cookie cutters or a sharp knife to make unique spooky faces and designs on each pumpkin.

How to Serve

These Jack-o’-Lantern Chocolate Sugar Cookies are perfect for any Halloween occasion. Serve them on a festive platter at your next Halloween party or pack them in treat bags for trick-or-treaters. They’re also a fun activity for a Halloween baking day with the kids – especially if you set up a decorating station with sprinkles, candies, and extra frosting. You can check out our easy Halloween snack mix for another party favorite. Enjoy!

That’s a Wrap

These Jack-o’-Lantern Chocolate Sugar Cookies are sure to be a hit this Halloween! They’re spooky, sweet, and oh-so-delicious. Perfect for parties, classroom treats, or a cozy night in. Now that you’ve mastered these festive cookies, why not explore our other delicious dessert recipes? I’d love to see your spooky creations! Share your photos with me on Facebook, Instagram, or Pinterest. Happy baking!