Filed Under: Cookies | Halloween

Jack-o’-Lantern Chocolate Sugar Cookies

Recipe By Tessa Arias
  |  
October 7th, 2021
5 from 2 votes
5 from 2 votes

How to make the most adorable Jack-o'-Lantern Cookies in time for Halloween! This recipe features my easy sugar chocolate cut out cookies with homemade cream cheese frosting. The cutest Halloween dessert.

Yield: 15 cookie sandwiches

Prep Time: 40 minutes

Cook: 9 minutes

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 more 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!!

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.

easy homemade sugar cookie dough in a mixing bowl

This is where these Jack-o’-Lantern chocolate sugar cookies come into play! They 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.

how to cut out jack o lantern shapes from chocolate cookie dough

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.

homemade jack o lantern cookies with orange cream cheese frosting for halloween

How to Make Jack-o’-Lantern Cookies

Ingredients for chocolate sugar cookies:

  • All-purpose flour – make sure to weigh your flour accurately. If you add too much flour, your cookies may end up dry and crumbly.
  • Dutch-process cocoa powder learn more about why Dutch-process is key to this recipe below.
  • Baking powder – this gives the cookies lift without adding too much spread so the cookies keep their shape.
  • Fine sea salt – so important to balance the sweetness!
  • Unsalted butter it’s important that your butter is at a cool room temperature, otherwise your cookies may spread into little puddles. Your sticks of butter should give slightly when pressed with your finger but still hold their shape. To be precise, your butter should be 67°F.
  • Granulated sugar – it wouldn’t be a sugar cookie without this!
  • Eggs – these are essential to forming a beautifully pliable dough and cookies that stay soft for days.
  • Vanilla extract – no sugar cookie recipe is complete without vanilla extract.

The BEST cocoa powder for chocolate cookies:

I opted for Dutch-process for a few important reasons. One, it has a high fat content so it’ll make for richer and softer cookies. Two, it has a less acidic chocolate flavor to complement the cream cheese filling perfectly. Three, it contributes a beautiful rich and 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 use natural unsweetened cocoa?

Yes, your cookies may just be drier in texture and lighter in color.

Tools for jack-o’-lantern cookies:

Tips for perfect Halloween cookies:

  1. 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!
  2. For perfect cut out jack-o’-lantern cookie shapes, make sure to get your free cookie cut out template here. I used this alongside the cookie cutter detailed above.
  3. Make sure the pumpkin shapes are nice and cold and firm before cutting out the eyes and mouth.
how to cut out shapes using a paring knife for jack o lantern halloween cookies
chocolate sugar cookies and jack o lantern cookies on a pan with parchment paper

How to make cream cheese frosting:

  1. 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.
  2. On low speed, gradually add in the sugar and beat until ultra smooth and creamy. Add more powdered sugar if needed for a stiffer consistency.
  3. Squeeze in a few drops of orange gel food coloring. Beat until frosting reaches desired color.
how to assemble a jack o lantern cookie sandwich

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 for cookies over silicone mats. Parchment is easier and quicker to cleanup. 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 these jack-o’-lantern chocolate sugar cookies:

Store 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?

Yes! The cookies alone keep particularly well. Store them 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.

bite taken out of a jack o lantern cookie

More Halloween recipe ideas:

5 from 2 votes

How to make
Jack-o’-Lantern Chocolate Sugar Cookies

Yield: 15 cookie sandwiches
Prep Time: 40 minutes
Cook Time: 9 minutes
Chilling time 1 hour 30 minutes
Total Time: 2 hours 19 minutes
How to make the most adorable Jack-o'-Lantern Cookies in time for Halloween! This recipe features my easy sugar chocolate cut out cookies with homemade cream cheese frosting. The cutest Halloween dessert.

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!)
  • Orange gel food coloring

Directions

Make the cookies:

  1. In a medium bowl, sift together the flour, cocoa powder, baking powder, and salt.
  2. 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.
  3. 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.
  4. 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.

  5. 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.

  6. 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.
  7. 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 5 days or in the freezer for up to 1 month.

Make the cream cheese frosting:

  1. 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:

  1. 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

You can use natural unsweetened cocoa powder instead of Dutch process, your cookies may just be drier in texture and lighter in color. 
Course: Dessert
Cuisine: American
Keyword: chocolate sugar cookies, halloween cookies, jack o lantern cookies

Photos by Joanie Simon | The Bite Shot

Tessa Arias

About Tessa...

I share trusted baking recipes your friends will LOVE alongside insights into the science of sweets. I'm a professionally trained chef, cookbook author, and cookie queen. I love to write about all things sweet, carb-y, and homemade. I live in Phoenix, Arizona (hence the blog name!)

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Recipe Rating




  1. #
    Jessica — October 18, 2021 at 9:41 am

    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.

    • #
      Emily — October 18, 2021 at 3:40 pm

      Yay! So happy to hear your entire family enjoyed baking and decorating these cookies together!

  2. #
    Rose — October 19, 2021 at 1:36 pm

    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!!

    • #
      Emily — October 20, 2021 at 12:05 pm

      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 🙂

  3. #
    Cindy — October 24, 2021 at 11:37 am

    Hi! I entered email fir template but have not received. Thx!
    Cindy

    • #
      Haley Wehner — October 25, 2021 at 9:42 am

      Hi Cindy – just sent you an email with a link to the guide!

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