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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!
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 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.
Reader Love
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!
The dough was easy to work with and spread very little. I couldn’t believe how soft and chewy the cookies turned out! I will definitely be adding this recipe to my cookie arsenal
Key Recipe Ingredients
Dutch-Process Cocoa Powder: I recommend this for its higher fat content, which helps create richer, softer cookies. It also gives the cookies a deeper color and less acidic chocolate flavor that pairs especially well with cream cheese frosting. You can substitute natural cocoa 1:1, but the cookies may be slightly drier and lighter in color. Learn more about the differences between natural and Dutch-process cocoa here.
Baking Powder: Helps the cookies rise slightly while keeping them tender and soft without losing their shape.
Cream Cheese: Creates a rich, tangy frosting that pairs perfectly with the chocolate cookies. Use full-fat brick-style cream cheese and not the spreadable kind.
Powdered Sugar: Sift the powdered sugar for the smoothest frosting.
Gel Food Coloring: Gel coloring is more concentrated than liquid food coloring, so you only need a few drops to create a vibrant orange frosting without adding excess liquid.
Tools for Jack-o’-Lantern Chocolate Sugar Cookies:
- Jack-o’-lantern cookie cutter – This cookie cutter set is so easy and fun to use!
- Light-colored aluminum baking sheets – Avoid dark nonstick pans altogether as they cook too aggressively and may burn the bottoms of your cookies.
- Sharp paring knife – for cutting out the jack-o’-lantern shapes (if you’re not using a cookie cutter).
- Icing spatula – I like this one from Ateco.
- Parchment paper – I prefer parchment over silicone baking mats for these cookies. Avoid dark baking sheets and nonstick cooking spray, which can cause the cookies to brown and spread too much.
No Cookie Cutter?
No problem! Use my free Jack-o’-lantern printable template here. You could also use my Easy Cookie Icing recipe to make the Jack-o’-Lantern design with icing instead!
Tips for Perfect Halloween Cut-Out Cookies
- Measure your flour correctly. Use a digital scale for the best results, or use the spoon-and-level method. Too much flour can make these cookies hard, dry, or crumbly.
- Don’t reduce the sugar. Sugar contributes more than sweetness, so reducing it can affect the texture. Learn more about how sugar works in baking here.
- Roll, chill, then cut. Roll the dough at room temperature, then chill the rolled sheets before cutting out the shapes. This makes the dough easier to work with and helps the cookies hold their shape.
- Chill before cutting the faces. Make sure the pumpkin shapes are cold and firm before cutting out the eyes and mouth.
Storage & Make ahead
Storage: Store unfrosted cookies in an airtight container at room temperature for up to 3 days. Once filled and frosted, store the cookie sandwiches at cool room temperature for up to 2 days. I don’t recommend refrigerating the frosted cookies as they can dry out faster.
Make-Ahead: The unfrosted cookies freeze especially well. Store in an airtight container in the freezer for up to 2 months, protecting them from getting damaged. Thaw at room temperature before filling and decorating. I have not tried freezing the fully assembled cookies.
Frequently Asked Questions
Yes. Natural can be substituted 1:1, but the cookies may be slightly drier and lighter in color.
Gel food coloring is best. Add a couple of drops at a time until you reach your desired color.
Yes! Use my free Jack-o’-lantern printable template here, or you could use my Easy Cookie Icing to decorate the cookies with a jack-o’-lantern design instead.
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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 or paring knife and template 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).
Notes
Photos by Joanie Simon.
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!