Halloween Pumpkin Cookies

5 from 2 votes

Halloween Pumpkin Cookies

Brown butter, warm spices, and pumpkin meet rich chocolate in these charming Spooky Halloween Pumpkin Cookies! Each soft cookie sandwich reveals a delightful surprise - chocolate ganache peeking through jack-o'-lantern faces!

Prep Time1 30

Cook Time35

Cooling time30

Total Time2 35

Course: Dessert

Cuisine: American

Diet: Vegetarian

Servings: servings

Calories: 373kcal

Author: Briana

Equipment

Ingredients

Soft pumpkin cut-out cookies

¾ cup unsalted butter
1 cup pumpkin puree 244 grams
2 ½ cups all purpose flour plus more for the working surface and to flour the cookie cutters 340 grams
1 tablespoon pumpkin pie spice
1 teaspoon kosher salt
1 teaspoon cinnamon
½ teaspoon baking soda
1 ½ cups brown sugar 300 grams
2 tablespoons maple syrup 30 ml
1 tablespoon vanilla extract
2 large egg yolks room temperature

Spiced sugar for rolling the cookies

¼ cup white sugar 50 grams
1 teaspoon pumpkin spice

Chocolate ganache

4 ounces chocolate wafers or chopped chocolate bars semi-sweet, dark chocolate, or milk chocolate, whatever you like
4 ounces heavy cream

Instructions

Prep the ingredients

Start by browning the butter. Here is our step-by-step guide on how to brown butter. Set it aside to cool in the fridge while you prep the other ingredients.
¾ cup unsalted butter
Meanwhile, place the pumpkin puree in a cheesecloth or paper towel in a metal sieve, and over a bowl to catch the excess liquid. You may need to use a few paper towels. Wring out ALL of the excess liquid!
1 cup pumpkin puree

Make the cookie dough

In a small bowl, whisk together the all-purpose flour, pumpkin spice, kosher salt, cinnamon, and baking soda. Set aside.
2 ½ cups all purpose flour, 1 teaspoon kosher salt, ½ teaspoon baking soda, 1 tablespoon pumpkin pie spice, 1 teaspoon cinnamon
In a large bowl, combine the cooled brown butter, vanilla extract, brown sugar, maple syrup, and drained pumpkin puree. Mix together until smooth and creamy with a hand mixer (or stand mixer with a paddle attachment) for about 5 minutes. The mixture should become pale and fluffy. Add in egg yolks and mix again until totally combined.
1 ½ cups brown sugar, 2 tablespoons maple syrup, 1 tablespoon vanilla extract, 2 large egg yolks
Add the dry ingredients to the wet, and mix to combine. Put onto a floured work surface, then divide the dough in half. Flatten each piece of dough between parchment paper. Roll the dough to be about ¼ to ⅓-inch thick. Quick note - the thicker the dough, the longer the cookies will take to bake! Then wrap the dough halves in plastic wrap. Chill in the fridge or freezer for about an hour so the dough can rest.

Make the cutouts

After the dough has chilled, working in batches (keeping half of the dough in the freezer while you work on one half) transfer the dough to a floured work surface. Flour your cookie cutters between each use, and make the pumpkin shapes. In half of the pumpkins, cut out jack-o-lantern faces. Place the cookies on a parchment-lined baking sheet and place them in the freezer to chill.
Meanwhile, re-roll the scraps and make more cutouts until you run out of dough! If the dough gets too sticky, place it back in the freezer for a few minutes to firm up. This recipe makes about 13-14 jack-o-lantern sandwich cookies, or roughly 26-28 cookies if you use the cookie cutters we did. You can make more or less easily depending on the size of your cookie cutters! Just be aware that this may impact the bake time.

Bake the cookies

When it's time to bake, preheat the oven to 350°F, add trays of cookies, and bake for 11-14 minutes until set. These cookies are VERY soft, and sometimes spread a little. If the mouth and eye shapes spread, use a toothpick or knife to make more room in the cutouts of the eyes.
Cool the cookies on the cookie tray until they have firmed up for about 5-7 minutes, then transfer to a wire cooling rack to cool completely.

Roll in spiced sugar

In a separate bowl or on a plate, combine white sugar and pumpkin spice or cinnamon. Place the cookies in the sugar mixture and toss to coat.
¼ cup white sugar, 1 teaspoon pumpkin spice

Make the chocolate ganache & assemble the cookies

To make the chocolate ganache, heat the heavy cream until it's very hot but NOT boiling, and pour it over top of the chocolate. Let it sit for about 3 minutes, then stir until the mixture is smooth. Allow the ganache to cool off and set for a few minutes, just so it doesn't run right off the cookies.
4 ounces chocolate wafers or chopped chocolate bars, 4 ounces heavy cream
On a solid half of a pumpkin (with no faces cut out), place a dollop of chocolate ganache in the center.
Place a jack-o-lantern cut out cookie over top of a cookie with chocolate ganache, and watch the chocolate press through to make an adorable spooky face!
Store assembled cookies in an airtight container in the refrigerator for up to a week.Yes! Freeze unfilled cookies for up to 3 months. Thaw and fill with ganache before serving.

Notes

Use a kitchen scale for best results. This is probably our top tip, every time! Using a kitchen scale makes all the difference for accurate measurements, that way, you don't end up with too much flour in the dough!

Make sure to get all the excess water out of the pumpkin puree. We recommend using a heavy-duty paper towel or cheesecloth to wring out all of the excess moisture. We don't want to add extra moisture to the cookie dough, since this dough is already on the wet side!

Let the brown butter cool. Make sure you give the butter time to chill, or else it will combine with the sugar and turn into a greasy mess. Place it in the fridge or freezer for a few moments to cool off completely before using.

Cream the wet ingredients well. This will really help the texture of your cookies and help prevent spreading.

Chill the dough, and keep your kitchen cold! You'll also want to work in batches to keep the dough cold while cutting out the shapes. This dough is more wet than a regular cut-out cookie (which makes them so soft and flavorful!) but it can be a little hard to work with when the dough gets warm! If the dough becomes too sticky, add a little flour, or return it to the freezer to get it to firm up again.

Use flour on the cookie cutter to help get cleaner cutout shapes. Between each use, we recommend using a floured cookie cutter to help the cuts be a little cleaner!

After you've cut out shapes, place the cutouts in the freezer while you preheat the oven. The longer the cutouts can freeze before baking, the better they will keep their shape.

If the cutout eyes and mouths spread while baking, use a toothpick or knife to reshape the jack-o-lantern shape while they are still warm.

Use an oven thermometer. Some ovens run hotter or cooler than the temperature dial states. We always recommend monitoring your oven's actual temperature by using an oven thermometer.

Cool completely. Since these cookies are so soft, they do need to cool completely before handling or you risk them falling apart. Let them cool for about 10 minutes on the baking sheet before transferring them to a cooling rack to finish cooling down completely.

Let the ganache cool slightly before assembling the cookie sandwiches to prevent running.

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