Tessa's Recipe Rundown
Taste: Just enough chocolate to balance the tang of the cream cheese filling.
Texture: The cookies are soft yet sturdy and the cream cheese is ultra smooth and creamy.
Ease: A little time-consuming to make and assemble but super fun and doable.
Why You’ll Love This Recipe: A festive treat that actually tastes good!
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These adorable Jack-o’-Lantern Chocolate Sugar Cookies are the best treat for your Halloween dessert table!
To be honest, Halloween isn’t my favorite food holiday. I think it’s because I’m not a big candy person. I’d take chocolate over candy (especially candy corn) all day, every day.
Despite that, when Hocus Pocus season rolls around, I still want to bake and enjoy something festive and fun.
This is where these Jack-o’-Lantern Chocolate Sugar Cookies come into play! These Halloween cookies have the perfect amount of chocolate flavor and stay soft for days. Sandwich them with a thick layer of festive orange cream cheese frosting and you’ll be wishing it were Halloween year-round.
In fact, you could totally remake this recipe for just about any holiday. All you’d need to do is switch up the cookie cutter shape and opt for a different shade of gel food coloring.
Sprinkle of Science
How to Make Jack-o’-Lantern Chocolate Sugar Cookies
How do I Make Soft, Chewy Chocolate Sugar Cookies? Avoiding Dry or Crumbly Cookies:
- Measure your flour correctly. I highly recommend using a digital scale, but using the spoon-and-level method works, too – learn more about correct measuring here. Accidentally mismeasuring your flour is the most common reason your cookies are hard, dry, or crumbly.
- Don’t reduce the sugar. Sugar does so much more than simply sweetening your cookies, so please don’t reduce the sugar in the cookies. Learn more about how sugar works in baking here.
- Use a high-quality cocoa powder. More on this just below.
The BEST Cocoa Powder for Chocolate Sugar Cookies
I opted for Dutch-process for a few important reasons. One, it has a high fat content so it’ll make for richer, softer cookies (more on cocoa powder fat content here). Secondly, it has a less acidic chocolate flavor, which complements the cream cheese filling perfectly. Thirdly, it contributes a beautifully rich, festive color.
Learn more about the differences between Natural Cocoa vs Dutch Process Cocoa Powder here.
I Don’t Have Dutch-Process Cocoa Powder – Can I Use Natural Unsweetened Cocoa Instead?
Yes, but your cookies may be slightly drier in texture and lighter in color. Learn more about cocoa powders here.
Tools for Jack-o’-Lantern Chocolate Sugar Cookies:
- Sifter – Don’t skip sifting the powdered sugar for the cream cheese frosting, otherwise you could end up with lumpy, gritty frosting.
- Jack-o’-lantern cookie cutter – This cookie cutter set is so easy and fun to use! You can also use my free Jack-o’-lantern printable template here.
- Sharp paring knife – for cutting out the shapes of your jack-o’-lantern.
- Icing spatula – I like this one from Ateco.
Can I Make These Cookies Without a Jack-o’-Lantern Cookie Cutter or Template?
Sure! Use my Easy Cookie Icing recipe to make the Jack-o’-Lantern design with icing instead!
Tips for Perfect Halloween Cut-Out Cookies:
- Roll out the dough when it’s at room temperature, then chill the sheets before cutting out shapes. This makes working with the dough so much easier and more enjoyable. Especially if you’re making them with kids!
- I used a homemade template made with parchment paper, but for perfect cut-out jack-o’-lantern cookie shapes, use a cookie cutter like this!
- Make sure the pumpkin shapes are nice and cold and firm before cutting out the eyes and mouth.
What Food Coloring Should I Use for the Cream Cheese Frosting?
- I highly recommend using gel food coloring over liquid dye.
- Liquid dyes add excess liquid to the frosting, making the frosting runny. Liquid food coloring also is not as concentrated, so you would need much more to color the frosting.
- Just add a couple of drops of gel dye at a time (they’re very concentrated!) and beat in until the frosting reaches your desired color.
What Kind of Baking Sheet is Best for Chocolate Sugar Cookies?
A light-colored aluminum half-sheet pan is my favorite for baking cookies. Avoid dark nonstick pans altogether as they cook too aggressively and may burn the bottoms of your cookies.
Check out my Baking Pans 101 post for all the surprising details. Or, just click here to score my favorite baking pans for cookies (and everything else!).
Should I Line my Baking Sheets with Parchment Paper or Silicone Baking Mats to Bake Cookies?
- I prefer parchment paper on my cookie sheet for cookies over silicone mats.
- Parchment is easier and quicker to clean up.
- Silicone mats like Silpats can actually lead to more spreading and browning. Check out my experiment on Silpats vs. parchment paper here.
- Whatever you do, never spray your baking sheet with nonstick cooking spray when baking cookies. This will lead to too much browning and spread (hello, burnt cookie puddles).
How to Store Jack-o’-Lantern Chocolate Sugar Cookies
Store Jack-o’-Lantern Chocolate Sugar Cookies in an airtight container at room temperature for up to 3 days. Once the cream cheese frosting is added, store at room temperature for up to 2 days. I don’t advise storing the frosted cookie sandwiches in the fridge as they will dry out faster.
Can These Cookies be Made Ahead of Time? How to Freeze Chocolate Sugar Cookies
Yes! The cookies alone keep particularly well. Store Jack-o’-Lantern Chocolate Sugar Cookies at room temperature as specified above, or you can also freeze them in an airtight container for up to 2 months. Just be sure they’re stored in a safe place where they won’t get damaged in the freezer.
More Halloween Recipes You’ll Love:
- Spooky Halloween Cookies
- Halloween Charcuterie Board
- Brown Butter Pumpkin Chocolate Chip Cookies
- Monster Cookie Bars
- Halloween Brownies
- Monster Cookies
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Ingredients
For the chocolate sugar cookies:
- 2 1/2 cups (318 grams) all-purpose flour
- 1/2 cup (50 grams)
Dutch-process cocoa powder * - 1 teaspoon baking powder
- 1/4 teaspoon fine sea salt
- 1 1/2 sticks (170 grams) unsalted butter, at cool room temperature
- 1 cup (200 grams) granulated sugar
- 2 large eggs, at cool room temperature
- 1 teaspoon pure vanilla extract
For the cream cheese frosting:
- 4 ounces (113 grams) cream cheese, at room temperature
- 4 tablespoons (57 grams) unsalted butter, at room temperature
- 2 teaspoons vanilla extract
- 1 1/2 cups (188 grams) powdered sugar, sifted (don't skip sifting!)
- A few drops of
Orange gel food coloring
Instructions
Make the cookies:
- In a medium bowl, sift together the flour, cocoa powder, baking powder, and salt.
- In a large bowl, use an electric mixer to beat the butter and sugar on medium-high speed until smooth and well combined, 1 to 2 minutes. Add the eggs, one at a time, until well combined. Add the vanilla extract. On low speed gradually add the flour mixture and beat until thoroughly combined.
- Place the dough in between two large pieces of parchment paper or silicone mats on a work surface. Roll the dough out to a 1/4-inch thickness. Chill in the refrigerator until firm, at least 1 hour, or in the freezer until firm, about 30 minutes.
- Line large baking sheets with parchment paper. Use a pumpkin cookie cutter to cut out shapes from the dough and place on prepared baking sheets. In half of the pumpkins, cut out the triangle eyes and mouth shape.
- Gently reroll remaining scraps of dough to a 1/4-inch thickness and repeat the process. If the sheet of dough softens too much at any point, place it back in the freezer or fridge until firm again before cutting and moving more shapes.
- Chill the baking sheets of cut cookie dough in the refrigerator for 30 minutes or freezer for 15 minutes, or until dough is firm. Meanwhile, preheat the oven to 350°F.
- Bake for 8 to 9 minutes, or until the cookies are set but not overbaked. Let cool on baking sheets for 5 minutes before removing to a wire rack to cool completely. Plain cookies can be stored in an airtight container at room temperature for up to 3 days or in the freezer for up to 2 months.
Make the cream cheese frosting:
- In the bowl of a stand mixer fitted with the paddle attachment, beat the cream cheese, butter, and vanilla on medium-high speed until very light, creamy, and smooth, about 2 to 3 minutes. On low speed, gradually add in the sugar and beat until fluffy, about 2 minutes more. Add in a few drops of orange gel food coloring until desired shade is reached.
Assemble the sandwiches:
- Place a dollop of cream cheese frosting on the center of the top of the plain pumpkin shaped cookies. Don’t frost the bottom side, otherwise the pumpkin stem shapes won’t line up. Place a jack o’lantern cookie on top of each, pressing down slightly to sandwich the filling. Serve or store in an airtight container at room temperature for up to 2 days (the sugar in the cream cheese frosting acts as a preservative, but they should not be stored at room temperature for longer than that).
I love so many of Tessa’s recipes but this one…not so much. Without a cookie cutter, cutting out the shapes was a pain and the 4” cookies were too big. Especially when you put two together. They probably would have been better with just one small cookie topped with her sugar cookie icing.
Super cute & delicious!
Delicious!! My dad said he could eat just the cookie by itself!
Just made this recipe and it’s great! It’s honestly one of the best cookies I’ve ever made.
This recipe was easy to follow and was a fun alternative to classic sugar cookies. I love the cream cheese filling and how it complements the chocolate cookies. They were delicious!
Very tasty and so cute!
Fun & tasty Halloween cookies! Rich chocolate cookie with cream cheese filling or frosting is a delicious combination.
Yummy and cute
Love this chocolate cookie recipe! Really easy and can be made into any shape. I will definitely make my next sandwich cookie smaller since each sandwich is already 2 cookies. It’s easiest to use with a paring knife while the dough is very cold for any cutouts.
For me, these weren’t the easiest to make as I am not that artistic, and my jack o lanterns came out a bit crooked, but they were delicious! Definitely would make them again as a cut out cookie, just not as a filled jack o lantern!
Loved making these! Simple, easy, fun … and very tasty!!
These came out so good!! A big hit with my family!