Name: Jack-o’-Lantern Chocolate Sugar Cookies
Prep time: 25 min
Cook time: 9 min
Total time: 2 h 5 min
Cuisine: American
Ingredients: 2 1/2 cups all-purpose flour; 1/2 cup Dutch-process cocoa powder; 1 teaspoon baking powder; 1/4 teaspoon fine sea salt; 1 1/2 sticks unsalted butter, at cool room temperature; 1 cup granulated sugar; 2 large eggs, at cool room temperature; 1 teaspoon pure vanilla extract; 4 ounces cream cheese, at room temperature; 4 tablespoons unsalted butter, at room temperature; 2 teaspoons vanilla extract; 1 1/2 cups powdered sugar, sifted; A few drops orange gel food coloring

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Jack-o’-Lantern Chocolate Sugar Cookies are a festive and fun Halloween treat that combines rich, soft chocolate cookies with a creamy orange-tinted cream cheese frosting. Sandwiched together with spooky jack-o’-lantern faces, these cookies are as delightful to look at as they are to eat—perfect for parties, gifting, or just getting into the Halloween spirit.

Why You’ll Love This Recipe

Festive and Fun: The jack-o’-lantern cutouts add a playful, seasonal touch to a classic sandwich cookie.
Rich Chocolate Flavor: Made with Dutch-process cocoa, the cookies are deeply chocolatey without being too sweet.
Creamy Frosting: The orange cream cheese frosting is smooth, slightly tangy, and balances the cocoa perfectly.
Make-Ahead Friendly: Both the cookies and frosting can be made in advance.
Customizable Designs: Use different cookie cutter shapes or colors for other holidays.

Ingredients

(Tip: You’ll find the full list of ingredients and measurements in the recipe card below.)

For the chocolate sugar cookies

2 1/2 cups all-purpose flour
1/2 cup Dutch-process cocoa powder
1 teaspoon baking powder
1/4 teaspoon fine sea salt
1 1/2 sticks unsalted butter, at cool room temperature
1 cup granulated sugar
2 large eggs, at cool room temperature
1 teaspoon pure vanilla extract

For the cream cheese frosting

4 ounces cream cheese, at room temperature
4 tablespoons unsalted butter, at room temperature
2 teaspoons vanilla extract
1 1/2 cups powdered sugar, sifted
A few drops of orange gel food coloring

Directions

Make the cookies

In a medium bowl, sift together flour, cocoa powder, baking powder, and salt.
In a large bowl, beat butter and sugar with an electric mixer on medium-high speed until smooth and fluffy (1–2 minutes).
Beat in the eggs one at a time, followed by the vanilla extract.
Reduce speed to low and gradually mix in the dry ingredients until fully combined.
Place dough between two sheets of parchment paper or silicone mats. Roll to 1/4-inch thickness and chill in the fridge for at least 1 hour, or in the freezer for 30 minutes.
Preheat oven to 350°F (177°C). Line baking sheets with parchment paper.
Use a pumpkin-shaped cookie cutter to cut out cookies. Cut jack-o’-lantern faces (eyes and mouth) into half of the shapes.
Reroll scraps and repeat as needed, chilling dough if it becomes too soft to work with.
Chill cut cookies on baking sheets in the refrigerator for 30 minutes or freezer for 15 minutes.
Bake for 8–9 minutes or until set. Cool on baking sheets for 5 minutes, then transfer to wire racks to cool completely.

Make the frosting

In a stand mixer fitted with a paddle attachment, beat the cream cheese, butter, and vanilla on medium-high speed until smooth and creamy (about 2–3 minutes).
Reduce speed to low, gradually add the sifted powdered sugar, and beat until fluffy (2 minutes).
Mix in a few drops of orange gel food coloring until desired color is reached.

Assemble the cookies

Place a dollop of frosting onto the center of the flat side of each plain pumpkin cookie.
Top each with a jack-o’-lantern cutout cookie and press gently to sandwich.
Serve immediately or store in an airtight container at room temperature for up to 2 days.

Servings and timing

Servings: About 18 sandwich cookies (36 single cookies)
Prep Time: 25 minutes
Chill Time: 1 hour 30 minutes (total)
Cook Time: 9 minutes
Total Time: About 2 hours 5 minutes

Variations

Colorful Frosting: Swap orange for green, purple, or black food coloring for variety.
Different Shapes: Use ghost, bat, or skull cookie cutters for a Halloween cookie platter.
Add Spices: Mix cinnamon or pumpkin spice into the dough for a seasonal twist.
Chocolate Filling: Replace cream cheese frosting with chocolate ganache or buttercream.
Gluten-Free Option: Use a 1:1 gluten-free flour blend in place of regular flour.
Mini Cookies: Make smaller sandwich cookies for bite-sized treats.
Sprinkle Edges: Roll the frosting edges in Halloween sprinkles before serving.
Stuffed with Candy: Add a piece of chocolate or candy in the frosting center for a surprise bite.
Make Single Cookies: Skip the sandwiching and simply frost each cookie.
Vegan Version: Use dairy-free butter and cream cheese alternatives and an egg replacer.

Storage/Reheating

Assembled cookies can be stored in an airtight container at room temperature for up to 2 days. For longer storage, refrigerate for up to 1 week. If freezing, store the cookies without frosting and assemble after thawing. Let frozen cookies come to room temperature before serving. Do not microwave.

FAQs

Can I make the dough ahead of time?

Yes, you can chill the dough for up to 2 days or freeze it for up to 3 months before cutting and baking.

Do I have to use Dutch-process cocoa?

Dutch-process cocoa provides a smoother, darker chocolate flavor, but natural cocoa powder can be substituted if needed.

Can I freeze the baked cookies?

Yes, freeze plain cookies for up to 2 months. Thaw and frost when ready to serve.

Is the frosting safe at room temperature?

Yes, the sugar in the cream cheese frosting helps preserve it for up to 2 days at room temp.

How do I keep the cookie shapes from spreading?

Chilling the dough before cutting and again before baking helps the cookies retain their shape.

Can I make these without the jack-o’-lantern cutouts?

Absolutely. Simply make full pumpkin shapes and frost the tops or sandwich them plain.

Can I color the frosting with liquid food coloring?

Gel food coloring is best for vibrant color without altering frosting texture, but a small amount of liquid food coloring can work.

Can I use store-bought frosting?

Yes, but the homemade cream cheese frosting offers better texture and flavor.

What can I use instead of a pumpkin cookie cutter?

Any Halloween-themed cutter will work—bats, ghosts, cats, etc.

Can I double this recipe for a party?

Yes, this recipe scales well. Just double all ingredients and chill the dough in batches.

Conclusion

Jack-o’-Lantern Chocolate Sugar Cookies are the ultimate Halloween treat—festive, flavorful, and full of charm. With rich chocolate cookies, vibrant orange frosting, and spooky cutouts, they bring the spirit of the season to life in every bite. Whether you’re hosting a party, baking with kids, or just looking to impress, these cookies are sure to be a crowd favorite.