Cookies & BarsNo. 3738 · The 2026 edition
Halloween Pumpkin Cookies
Create adorable jack-o-lantern cookies with a hidden chocolate surprise that oozes through the cutouts.
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These Halloween pumpkin sandwich cookies feature a soft, spiced pumpkin dough filled with rich chocolate ganache. The tops are cut with jack-o-lantern faces, and when assembled, the ganache peeks through for a fun, spooky effect. Perfect for sharing at autumn parties or as a festive treat.
Ingredients
Directions
- Brown the butter, then let it cool in the refrigerator while you prepare the other components.
- Press the pumpkin puree through a cheesecloth or paper towels in a sieve over a bowl to remove excess moisture. Squeeze out as much liquid as possible.
- In a small bowl, whisk together the all-purpose flour, pumpkin pie spice, kosher salt, cinnamon, and baking soda. Set aside.
- In a large bowl, combine the cooled browned butter, vanilla extract, brown sugar, maple syrup, and drained pumpkin puree. Beat with a hand mixer or stand mixer with paddle attachment for about 5 minutes until pale and fluffy. Add the egg yolks and mix until fully incorporated.
- Add the dry ingredients to the wet and mix until combined. Turn the dough out onto a floured surface and divide in half. Flatten each piece between parchment paper and roll to about ¼ to ⅓ inch thick. Wrap each half in plastic wrap and chill in the fridge or freezer for about 1 hour.
- After chilling, work with one dough half at a time (keep the other in the freezer). Transfer to a floured surface. Flour your pumpkin-shaped cookie cutters between cuts. Cut out pumpkin shapes; on half of them, cut out jack-o-lantern faces. Place the cut cookies on a parchment-lined baking sheet and freeze.
- Reroll the dough scraps and continue cutting shapes until all dough is used. If the dough becomes sticky, pop it back in the freezer to firm up. This recipe yields about 13 to 14 jack-o-lantern sandwich cookies (26 to 28 individual cookies) depending on cutter size. Adjust bake time if your cookies are larger or smaller.
- Preheat the oven to 350°F. Bake the cookies in batches for 11 to 14 minutes, until set. They are very soft and may spread slightly. If the face cutouts close up, use a toothpick or knife to reopen them while the cookies are still warm.
- Let the cookies cool on the baking sheet for 5 to 7 minutes until firm, then transfer them to a wire rack to cool completely.
- In a separate bowl or plate, combine the white sugar and pumpkin spice (or cinnamon). Toss the cooled cookies in the sugar mixture until evenly coated.
- To make the chocolate ganache, heat the heavy cream until very hot but not boiling. Pour it over the chocolate wafers or chopped chocolate and let sit for about 3 minutes. Stir until smooth. Let the ganache cool slightly so it thickens but is still spreadable.
- Take a solid pumpkin cookie (without face cutouts) and place a dollop of ganache in the center.
- Press a jack-o-lantern cutout cookie on top of the ganache-topped cookie. The chocolate will squeeze through the face openings, creating a adorable spooky design.
- Store assembled cookies in an airtight container in the refrigerator for up to one week. Unfilled cookies can be frozen for up to 3 months; thaw and fill with ganache before serving.
Per serving
- 17.0 fat g
- 52.0 carbs g
- 32.0 sugar g
- 373.0 calories
- 4.0 protein g
More photos
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