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.
Pros: A festive treat that actually tastes good!
Cons: Cutting out the eyes and mouth shape can be a bit tricky, which is why we’ve put together a free template download.
Would I make this again? Yes!!
This post may contain affiliate links. Read our disclosure policy.
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.
These are sure to be a hit with your guests at any Halloween party! No tricks, just treats. 😉
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 that 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 that here.
- Use a high-quality cocoa powder. Learn more about 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. 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?
Yes, but your cookies may just be 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.
- Pumpkin cookie cutter kit – feel free to experiment with other Halloween shapes too, if you’d like.
- Jack-o’-lantern cookie cutter template – get your FREE cookie cut out template HERE. You can also use this plain pumpkin cookie cutter alongside the template for ease.
- 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!
- For perfect cut-out jack-o’-lantern cookie shapes, make sure to get your free cookie cut-out template here – or to make it even easier, 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 the details 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 Jack-o’-Lantern Chocolate Sugar Cookies be Made Ahead of Time? How to Freeze These 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:
- Double Chocolate Halloween Cookies
- Leftover Halloween Candy Cheesecake
- Halloween Charcuterie Board
- Brown Butter Pumpkin Chocolate Chip Cookies
- Loaded Cookie Bars
Check out ALL my Halloween recipes here!
Become a Baking Genius!
Sign up for our free email newsletter for NEW recipes & baking science secrets.
Jack-o’-Lantern Chocolate Sugar Cookies
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 3 or 4-inch pumpkin cookie cutter to cut out shapes from the dough and place on prepared baking sheets. Use a small paring knife to carefully cut out the triangle eyes and mouth shapes in half of the pumpkins.**
- Gently reroll remaining scraps of dough to a 1/4-inch thickness, cut out eyes and mouths in half of the pumpkins, and place on prepared baking sheets. 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).
Recipe Notes
October 2022 Baking Challenge
This recipe was the October 2022 selection for our monthly baking challenge! Every month you can join the challenge by baking the recipe and snapping a photo for a chance to win prizes! Learn more about my monthly baking challenges here. Check out everyone’s cookies:
These turned out perfectly! I’m not a huge chocolate cookie fan, but everyone at work loved them! Recipe was easy to make.
Delicious and adorable! Great holiday treat
I don’t normally make roll out cookies , but these were so much fun! My cutting could use some practice, but they turned out ok. They taste delicious! I love the filling!!!
Super easy to make and delicious!
Amazing taste for the cookie and loved the cream cheese frosting with it!
These were so fun to make! The dough was tricky to work with when it was warm, so plan accordingly for needing to pull it in and out of the freezer as Tessa suggests. I prefer a slightly thicker cream cheese frosting, but that is just personal preference. Otherwise, the cookie is amazing and they are so fun for a little more time intensive Halloween baking project!
absolutely loved these cookies!! everyone in my house loved them. they were super easy! the cream cheese frosting complimented the cookies so good!
These cookies are sure to be a showstopper at your Halloween party! The cookie dough comes together easily and the templates help to make the faces uniform. I will be making these all Halloween season!
Made these with two of my grandchildren. I had the dough ready and they cut out the pumpkin shape. My 8 year old granddaughter cut out the faces for the Jack-o-lantern, free-handed. They both mixed and colored the icing. The cookies were delicious and good memories were made!
I bet they had a blast baking these festive cookies with you, Jean! How wonderful! SO glad to hear this.
Hi! I entered email fir template but have not received. Thx!
Cindy
Hi Cindy – just sent you an email with a link to the guide!
I love these cookies! Don’t skip the Dutch chocolate. I think that is what makes these so good. They’re soft and not too sweet. I will definitely make these again!!
Yes, the dutch cocoa is definitely important in this recipe to ensure richer and softer cookies (rich color too!), I’m so happy you loved these cookies, thanks so much for sharing 🙂
These cookies are yummy and even with the icing they are not sickeningly sweet. They’re just right. My husband and daughter who normally do not like very sweet actually love these. They also loved helping make them too.
Yay! So happy to hear your entire family enjoyed baking and decorating these cookies together!