Nothing says Halloween like these Chocolate Jack-O-Lantern Linzer Cookies filled with a deliciously tart cherry jam. These cookies are so rich and chocolatey, perfectly tart from the filling, and dusted with confectioner’s sugar to complete the perfect cookie for the season of Halloween.

A tray of Halloween-themed chocolate cookies dusted with powdered sugar, shaped and decorated like carved Jack-o'-lantern pumpkins, surrounded by small, real pumpkins. The cookies have various facial expressions, from happy to spooky.

How To Make Chocolate Jack-O-Lantern Cookies

1. Prepare two cookie sheets by placing parchment paper on each. Set aside.
2. In a medium-sized bowl, whisk together the flour, cocoa powder, baking soda, and salt. Set aside.
3. In a separate, larger bowl or in the bowl of a stand mixer fitted with the paddle attachment, cream together the butter and sugar. Scrape down the sides of the bowl as you go. Cream the mixture until light and fluffy, about 2 minutes.
4. Add the eggs and vanilla to the butter mixture and continue to mix on low speed, scraping down the sides of the bowl as needed.
5. Once all the wet ingredients are evenly combined, add the dry ingredients to the wet mixture. Mix until a dough starts to form, then scrape down the sides of the bowl and finish mixing until everything is well combined.
6. Split the dough in half, then roll each portion evenly between two pieces of parchment paper to about 1/8″-1/4″ thick. This prevents sticking and makes for easy transfer. Transfer the dough to a cookie sheet and chill for about 1 hour.
7. Preheat the oven to 350°F once the dough has chilled.
8. Cut out as many pumpkin shapes as you can, rerolling the scraps until all the dough is used. If the dough becomes too soft, transfer it to the fridge as needed to keep it firm and easy to work with.
9. Use a small knife to cut out Jack-O-Lantern faces on half of the cookies. Place the cookies onto the prepared cookie sheets about 1 1/2″ apart. They will not spread much.
10. Bake for 8-9 minutes. Allow the cookies to cool completely on a wire rack before decorating.
11. Once the cookies have cooled, dust powdered sugar on top of each cookie with a Jack-O-Lantern face cut out.
12. Spread or pipe about 2-3 tsp of cherry jam on a cooled, uncut cookie, then top with another cookie with a face cut out. Repeat this step for each cookie.
13. Enjoy your spooky, delicious treats!

A hand holds a black Halloween-themed cookie shaped like a jack-o'-lantern and dusted with powdered sugar. More similar cookies and a small orange pumpkin are in the blurred background.

How to Store Chocolate Jack-O-Lantern Linzer Cookies

To keep your Chocolate Jack-O-Lantern Linzer Cookies fresh and delicious, follow these storage tips:
Room Temperature: Store the cookies in an airtight container at room temperature for up to one week. Keep them in a cool, dry place away from direct sunlight.
Refrigeration: If you prefer to store them for a longer period, refrigerate the cookies in an airtight container for up to two weeks.
Freezing: For extended storage, you can freeze the cookies. Place them in a single layer on a baking sheet to freeze individually, then transfer them to a freezer-safe bag or container. They can be frozen for up to three months. Thaw at room temperature before serving.

A stack of sliced chocolate cookies filled with jam sits on a black tray. The cookies are dusted with powdered sugar and shaped like spooky Halloween faces. The tray is decorated with cobweb-like material, and a small pumpkin is in the background.

Filling Alternatives

Raspberry Jam: For a classic Linzer cookie taste.
Apricot Jam: Adds a sweet and slightly tart flavor.
Nutella: For a rich, chocolatey twist.
Peanut Butter: For a savory and sweet combination.
Caramel Sauce: Adds a gooey and indulgent filling.

A hand holds a pumpkin-shaped chocolate cookie dusted with powdered sugar. The cookie has a carved jack-o'-lantern face. In the background, there are similar cookies and a small orange pumpkin. The scene evokes a Halloween theme.

Recipe Tips

Chilling the Dough: Chilling the dough makes it easier to work with and helps the cookies hold their shape during baking.
Cutting Shapes: Use a sharp knife or cookie cutter to create clean shapes. If the dough becomes too soft, chill it again before continuing.
Decorating: Dusting the top cookies with powdered sugar before assembly gives them a beautiful finish. Use a fine-mesh sieve for even coverage.
Spreading the Jam: Make sure the cookies are completely cooled before spreading the jam to prevent it from melting and making the cookies soggy.

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