Save
This chocolatey twist on traditional sugar cookies transforms into adorable jack-o'-lantern sandwich cookies that bring festive Halloween spirit to your dessert table. The rich cocoa-infused cookies paired with vibrant orange cream cheese frosting creates a treat that's as fun to make as it is to eat.
I first made these for my niece's Halloween party, and they disappeared faster than any other treat. Now they've become our annual tradition, with the kids eagerly waiting to help cut out the jack-o'-lantern faces.
Ingredients
- All-purpose flour: forms the foundation of these cookies providing the perfect structure
- Dutch-process cocoa powder: gives these cookies their deep chocolate flavor and gorgeous dark color
- Baking powder: provides just enough lift without losing the defined cookie edges
- Fine sea salt: balances the sweetness and enhances the chocolate flavor
- Unsalted butter: at cool room temperature ensures proper creaming with sugar
- Granulated sugar: provides sweetness and helps create the cookie's texture
- Large eggs: bind everything together and add moisture
- Pure vanilla extract: adds warmth and depth to the chocolate flavor
- Cream cheese: creates a tangy base that balances the sweet cookies perfectly
- Unsalted butter: adds richness and helps stabilize the frosting
- Vanilla extract: complements both the chocolate cookies and orange color theme
- Powdered sugar: sweetens and thickens the frosting to sandwich-worthy consistency
- Orange gel food coloring: transforms ordinary frosting into festive Halloween filling
Step-by-Step Instructions
- Prepare the cookie dough:
- Mix the dry ingredients thoroughly by sifting flour, cocoa powder, baking powder, and salt together. This critical step prevents cocoa lumps and ensures even distribution of leavening. Take your time with this process as it directly impacts the final texture.
- Cream butter and sugar:
- Beat the butter and sugar until the mixture becomes noticeably lighter in color and fluffier in texture. This incorporates air into the dough which helps create the perfect cookie texture. Avoid overbeating which can cause spreading.
- Add wet ingredients:
- Incorporate eggs one at a time allowing each to fully integrate before adding the next. This gradual addition prevents curdling and ensures a smooth dough. Add vanilla extract to enhance the chocolate flavor profile.
- Combine wet and dry ingredients:
- Gradually add the flour mixture to the butter mixture at low speed to prevent flour dust clouds and overworking the dough. Mix just until no dry streaks remain for tender cookies.
- Roll and chill the dough:
- Place dough between parchment or silicone mats and roll to even thickness. Chilling the rolled dough rather than a ball saves time and ensures consistent thickness throughout. The cold dough will hold its shape better during cutting and baking.
- Cut and shape:
- Use a pumpkin cookie cutter for all cookies then create jack o lantern faces in half the batch. Work efficiently with chilled dough to maintain crisp edges. Return dough to refrigerator if it becomes too soft to handle properly.
- Final chilling and baking:
- Chill cut cookies again before baking to ensure they maintain their shape in the oven. Bake just until set but not browned or dried out. Watch carefully during the last minute as chocolate cookies can easily overbake without showing obvious color changes.
- Prepare the frosting:
- Beat cream cheese and butter until completely smooth with no lumps remaining. Gradually add sifted powdered sugar to prevent a grainy texture. Add orange coloring incrementally until you achieve the perfect pumpkin shade.
- Assemble the sandwiches:
- Apply frosting to the plain pumpkin cookies and top with the cut out faces. Press gently to adhere without squeezing out the filling. The contrasting orange against the dark chocolate creates a striking visual effect.
Save
Dutch process cocoa is my secret weapon in these cookies. Its rich color creates the perfect backdrop for the jack o lantern faces to stand out. The first time I served these at our neighborhood Halloween party, even the adults were fighting over the last cookie. That moment cemented these as our signature Halloween treat.
Make Ahead Options
These cookies are perfect for advance preparation. The dough can be made up to 3 days ahead and stored wrapped in the refrigerator. You can also freeze the dough for up to a month. Already baked unfrosted cookies keep well in an airtight container for several days or freeze beautifully for up to 2 months. The cream cheese frosting can be made 2 days ahead and refrigerated, though you'll need to bring it to room temperature and briefly rewhip before using.
Ingredient Substitutions
If you cannot find Dutch process cocoa, natural unsweetened cocoa powder works but expect a slightly lighter color and different texture. For a dairy free option, substitute plant based butter and cream cheese alternatives in equal amounts. The cookies themselves can be made with a one to one gluten free flour blend for those with gluten sensitivities. If cream cheese isn't available, buttercream frosting works beautifully as an alternative filling, though you'll lose some of that tangy contrast.
Halloween Party Presentation
Elevate your cookie presentation by creating a spooky graveyard scene. Stand the cookie sandwiches upright in a bed of chocolate cookie crumbs to resemble pumpkins in a patch. Add green frosting vines between cookies and sprinkle with edible shimmer dust for a magical glow effect. For an interactive dessert table, provide plain cookies, frosting, and decorating tools so guests can create their own jack o lantern faces. These cookies also make adorable packaging when wrapped individually in clear cellophane with a black ribbon.
Recipe FAQs
- → Can I make these cookies ahead of time?
Yes! You can prepare the dough up to 3 days in advance and store it refrigerated. The unfrosted cookies can be frozen for up to 2 months. Once assembled with frosting, the cookies are best enjoyed within 2 days when stored at room temperature.
- → What if I don't have Dutch-process cocoa powder?
You can substitute natural unsweetened cocoa powder, though the cookies may be slightly drier in texture and lighter in color. The flavor will still be delicious, just with a slightly different chocolate profile.
- → Can I use regular food coloring instead of gel food coloring?
Gel food coloring is preferred because it provides vibrant color without thinning the frosting. If using liquid food coloring, you may need to add more powdered sugar to maintain the proper consistency.
- → Why do I need to chill the dough?
Chilling is crucial for this dough as it firms up the butter, making the cookies easier to cut cleanly and helping them maintain their shape during baking. Don't skip this step for best results.
- → How can I get clean cut-outs for the jack-o'-lantern faces?
Use small, sharp cookie cutters or a small paring knife for the facial features. Working with well-chilled dough is essential, and if the dough becomes too soft while cutting, return it to the refrigerator to firm up again.
- → Can these cookies be made without the cream cheese filling?
Absolutely! The chocolate cookies are delicious on their own or can be decorated with royal icing or chocolate ganache instead of the cream cheese filling. You can still cut out the faces for a festive look.