Jack-o'-Lantern Chocolate Sugar Cookies

By Emmy
April 15, 2025
These delightful Jack-o'-Lantern Chocolate Sugar Cookies combine rich chocolate flavor with a creamy frosting, making them the perfect Halloween treat. Easy to make and fun to decorate, they're sure to be a hit at any gathering. You've got to try this one!
Jack-o'-Lantern Chocolate Sugar Cookies
Servings 15 People
Calories 150 Kcal
Prep Time 40 M
Cook time 9 M
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Get ready for a spooktacular treat! These Jack-o'-Lantern Chocolate Sugar Cookies are not only delicious but also a fun way to celebrate Halloween. With a rich chocolate flavor and creamy frosting, they’re sure to delight everyone!

Tips for Success

Make sure to chill your dough properly for the best texture. And don’t worry if your cookies don’t look perfect; they’ll still taste amazing!

Favorite Parts

This part’s so satisfying: cutting out those pumpkin shapes and decorating them with frosting!

Ingredients

  • For the chocolate sugar cookies:
  • For the cream cheese frosting:

Instructions

  • Make the cookies:
  • Step 1
    - Sift dry ingredients: In a medium bowl, sift together the flour, cocoa powder, baking powder, and salt.
  • Step 2
    - Mix wet ingredients: 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.
  • Step 3
    - Chill dough: 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.
  • Step 4
    - Cut cookies: 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.
  • Step 5
    - Reroll scraps: 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.
  • Step 6
    - Chill cut cookies: 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.
  • Step 7
    - Bake cookies: 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:
  • Step 8
    - Beat frosting ingredients: 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:
  • Step 9
    - Frost cookies: 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).

Nutrition

  • Calories: 150, Fat: 7g, Carbs: 21g, Protein: 2g

Cooking techniques

Chilling the dough is key to achieving the perfect cookie texture. Be patient when cutting out shapes!

Variations or substitutions

Try using different cookie cutters for various shapes or flavors of frosting to match your occasion!

Storage tips

Store plain cookies in an airtight container at room temperature for up to 3 days or freeze for up to 2 months. Frosted cookies can be kept at room temperature for up to 2 days.

Notes

For a fun twist, add sprinkles or edible glitter to the frosting!

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"Well hey there, sugar! I’m Emmy, but most folks just call me Memaw. I’ve been cookin’ since I was tall enough to reach the stovetop — and let me tell you, there’s nothin’ that makes me happier than feedin’ folks good food made with love. Around here, we keep it simple, soulful, and downright delicious. So grab a plate, pull up a chair, and let’s get to cookin’!"