Jack-o’-Lantern Chocolate Sugar Cookies - Halloween and Fall Stuffed Cookies Idea

Move over boring Halloween candy—because these Jack O Lantern Cookies are about to steal the spotlight! Imagine soft, chocolatey cut-out cookies sandwiched with silky cream cheese frosting and carved into little pumpkin faces. Yep, they’re basically the dessert version of carving pumpkins—except way cuter and way more delicious.

So, how to make Jack-o-lantern cookies that are both Insta-worthy and melt-in-your-mouth good? Start with a base of my easy chocolate sugar cookie dough. It’s rich enough to balance the tangy cream cheese filling, yet sturdy enough to hold its shape. Once baked, you’ll cut out spooky pumpkin faces, spread that dreamy frosting, and assemble them into the most festive treat of the season. Stuffed Jack O Lantern Cookies may sound tricky, but trust me—they’re actually super doable (and fun!).

The best part? These little pumpkins deliver on more than just looks. The chocolatey bite hits you first, then comes the smooth frosting filling—basically the perfect blend of flavor and texture. If you’ve ever been disappointed by dry Halloween chocolate chip cookies or overly sweet treats, consider this your redemption recipe. IMO, these are the ultimate upgrade from the usual chocolate chip cookies stuffed with chocolate.

And yes, I know what you’re thinking—aren’t “stuffed” recipes usually savory, like stuffed bell peppers with jack-o'-lantern faces or those clever Jack O Lantern stuffed peppers floating around Pinterest? Exactly! That’s why these fall stuffed cookies are such a genius twist. You get the same seasonal, pumpkin-carved vibe… without having to eat vegetables (you’re welcome).

Bottom line: these cookies aren’t just cute—they’re crazy good. A little extra time in the kitchen means you’ll end up with the cutest Halloween dessert ever. So grab your cookie cutters, channel your inner pumpkin carver, and get baking. 

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Jack-o’-Lantern Chocolate Sugar Cookies - Halloween and Fall Stuffed Cookies Idea

These festive Jack-o’-Lantern sandwich cookies are the ultimate Halloween bake! You’ll start with rich chocolate sugar cookies, then fill them with tangy cream cheese frosting that’s dyed a playful pumpkin-orange. Cute, fun, and absolutely irresistible.

Yield: About 15 cookie sandwiches

Prep Time: 40 minutes

Chill Time: 1 hour 30 minutes

Bake Time: 9 minutes

Total Time: 2 hours 19 minutes

Author: Aleda

Category: Cookies

Ingredients

Chocolate Cookies:

• 2 1/2 cups (318 g) all-purpose flour
• 1/2 cup (50 g) Dutch-process cocoa powder
• 1 teaspoon baking powder
• 1/4 teaspoon fine sea salt
• 1 1/2 sticks (170 g) unsalted butter, cool room temperature
• 1 cup (200 g) granulated sugar
• 2 large eggs, cool room temperature
• 1 teaspoon vanilla extract

Cream Cheese Frosting:

• 4 oz (113 g) cream cheese, softened
• 4 Tbsp (57 g) unsalted butter, softened
• 2 teaspoons vanilla extract
• 1 1/2 cups (188 g) powdered sugar, sifted
• Orange gel food coloring, a few drops

Directions

1. Step 1: Prepare the dough
   Whisk the flour, cocoa, baking powder, and salt together in a medium bowl. In a separate large bowl, beat butter and sugar with an electric mixer until light and fluffy, about 1–2 minutes. Mix in the eggs, one at a time, then add vanilla. Reduce the speed and slowly incorporate the dry ingredients until everything comes together into a dough.
2. Step 2: Roll and chill
   Sandwich the dough between parchment sheets or silicone mats and roll it out to about 1/4-inch thickness. Transfer the sheet of dough to the fridge for 1 hour (or the freezer for 30 minutes) until firm.
3. Step 3: Cut shapes
   Line baking sheets with parchment. Cut out pumpkin shapes with a cookie cutter, then use a small knife or cutter to carve triangle eyes and mouths into half of them. Gather and reroll scraps as needed, keeping the dough chilled if it gets too soft. Chill cut cookies for another 30 minutes (or 15 in the freezer) while preheating the oven to 350°F (175°C).
4. Step 4: Bake
   Bake cookies for 8–9 minutes, until set but not dry. Allow them to rest on the baking sheet for 5 minutes before moving to a wire rack to cool fully. Store plain baked cookies in an airtight container for up to 3 days, or freeze for 2 months.
5. Step 5: Make the frosting
   Beat cream cheese, butter, and vanilla together in a stand mixer until creamy and smooth, about 2–3 minutes. Gradually mix in the sifted powdered sugar until fluffy. Tint with orange food coloring.
6. Step 6: Assemble
   Spread frosting on the flat side of a plain pumpkin cookie. Top with a cut-out Jack-o’-Lantern cookie, pressing lightly so the frosting peeks through the eyes and mouth. Repeat with the rest. Enjoy immediately, or store at room temperature (in an airtight container) for up to 2 days.

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