chocolate thumbprint cookie spiders with caramel spider webs

We are one week away from Halloween – are you prepared? Is your candy bowl stocked? Is your costume ready? These spooky chocolate thumbprint cookie spiders with caramel spider webs are perfect for Halloween parties.

Chocolate Thumbprint Cookie Spiders | Pass the Cookies |

Chocolate Thumbprint Cookie Spiders | Pass the Cookies |

Earlier this month I had a vivid dream that I was working late on October 31st and realized at 7pm that, not only was I not home to answer the door and hand out candy, but we also didn’t have a single piece of candy to give to trick-or-treaters. I ran to the store and the candy shelves were completely empty except for a few bags of M&Ms, which, of course, are of no use on Halloween. Needless to say, I woke up and immediately wrote “bags of Halloween candy” on our grocery list, to ensure that my dream did not become reality. If it was acceptable, I would hand out these cookies to everyone who comes to the door (they are too good not to share!), but I’ll stick to parties and potlucks for now.

Chocolate Thumbprint Cookie Spiders | Pass the Cookies |

Chocolate Thumbprint Cookie Spiders | Pass the Cookies |

Chocolate Thumbprint Cookie Spiders | Pass the Cookies |

The deep dark chocolate cookies deliver a rich flavor that is satisfying enough to stop at one, but so delicious that you want to go back for another anyway. The soft inside of the cookie contrasts with the crunchy exterior coated in turbinado sugar. In addition to adding a crunch, the coarse sugar makes the cookies sparkle on the serving platter. I brought some of these cookies on a family road trip a few weeks ago and they were gone instantly. My dad declared them the best chocolate cookie he has ever had, and even my mom, who claims to not like chocolate cookies, was asking for her share of the treat. How can you not love a thumbprint as cute as these?

Chocolate Thumbprint Cookie Spiders | Pass the Cookies |

Chocolate Thumbprint Cookie Spiders | Pass the Cookies |

Chocolate Thumbprint Cookie Spiders | Pass the Cookies |

The amber caramel spider webs are a fun and totally optional addition, and add a bonus treat to your display. After swirling the liquid caramel around to make spider web shapes, the burnt sugar webs become hardened caramel snacks that pair amazingly with the dark chocolate thumbprint cookies. They make gorgeous, shiny, edible decorations that pop against the almost-black thumbprints and make the dessert even spookier.

Chocolate Thumbprint Cookie Spiders | Pass the Cookies |

Chocolate Thumbprint Cookie Spiders | Pass the Cookies |

Homemade hard caramels and dark chocolate cookies – these are the grown-up version of Halloween, and I’m a-okay with that.

Chocolate Thumbprint Cookies
1 cup (2 sticks) butter, at room temperature
1 1/3 cups sugar
2 eggs
2 tablespoons milk*
1 teaspoon vanilla
2 cups flour
1 cup dark cocoa powder
1 teaspoon sea salt

For assembly (optional)
¼ cup chocolate chips, melted
pretzel sticks (not shown, but another option for spider legs)
Candy eyeballs

*You can use any milk you prefer. I tried skim milk, cream, and plant-based milk and noticed no difference in the cookies.

Caramel Spider Webs
½ cup granulated sugar
2 tablespoons cold water

To make the chocolate thumbprint cookies
In the bowl of an electric mixer fitted with the paddle attachment, beat the butter on medium speed for 10-20 seconds. Add the sugar and beat for another 4-5 minutes, until the mixture is pale and fluffy. Scrape down the sides of the bowl with a spatula.

In a medium bowl, whisk the cocoa powder, then add four and salt and whisk again. Whisking the cocoa powder first helps you get all clumps out of the powder before it gets mixed with flour. Set aside.

In a small bowl, lightly whisk together the eggs, milk, and vanilla. Add the liquid ingredients to the butter-sugar mixture and mix for about 10-20 seconds, until the mixture resembles cottage cheese. Scrape down the sides of the bowl and mix again on medium-speed for about 30-45 seconds, until the mixture is fully incorporated and the texture is uniform.

Add the dry ingredients to the batter and mix on low speed until the dough comes together, about 30 seconds. Scrape down the sides of the bowl and mix on medium speed until fully combined. Cover bowl with plastic wrap and refrigerate until firm (about 3 hours).

Preheat the oven to 350 degrees F and line a few baking sheets with parchment paper. Scoop the chilled dough into 1 ½-tablespoon balls, about the size of a golf ball. I used my medium cookie scoop for this. Roll the dough balls in turbinado sugar and place them a few inches away from each other on your prepared trays. Press your thumb or pointer finger gently into the middle of the balls to slightly flatten and form a small indention in the cookie. Bake for 12-15 minutes, rotating the pans halfway through. The cookies should be set and have small cracks on their tops.

Chocolate thumbprint cookies can be stored in an airtight container at room temperature for a few days. The dough can be frozen for a few weeks. If you want to freeze the dough, scoop it into balls, roll the balls in turbinado sugar, place them on a parchment-lined cookie sheet, and freeze the cookie sheet for 1 hour. After an hour, remove the cookie sheet from the freezer, place the frozen cookie dough balls in a gallon-sized zippered freezer bag and freeze until you want to bake them. They can be baked from frozen, though you may need to add an extra minute or two to the baking time.

To make the caramel spider webs
In a small saucepan, stir the sugar and water together. Bring to a boil over medium-high heat and cook until the mixture starts to turn amber around the edges, about 5 to 8 minutes.

Gently swirl the pan to even out the color and prevent the sugar from burning in isolated spots. Continue to cook the mixture until the sugar turns medium amber, about 30 more seconds. Once the caramel begins to turn amber it will darken very quickly, so keep an eye on it.

Line a baking sheet with parchment paper. Working quickly, scoop up some caramel with a spoon and drizzle it onto the sheet in the shape of spider webs – I started by making an asterisk then swirled circles and spirals on top of those. I find it easier to do one spider web at a time, rather than all of the asterisks followed by all of the spirals and circles. If your designs are too thin they will be very delicate and may break. Try to make sure they have enough caramel to easily hold their shape. Let the caramel webs cool completely (about 10-20 minutes). When you are ready to serve the cookies, gently remove the caramel webs from the cookie sheets with a metal spatula. If they are difficult to remove, lift the parchment paper and carefully press the web from the bottom, or twist the pan as you would a tray of ice cubes to loosen all of the caramel decorations. The caramel shapes will store in an airtight container for a few days.

To assemble the spiders
Place the melted chocolate in a small zippered bag or a pastry bag. Pipe the chocolate into stripes and zigzags onto a parchment lined baking sheet. Let the chocolate cool completely (this could take a while, depending on the temperature of your kitchen. You can also place them in the fridge to speed up the cooling process. (Note: these chocolate legs are very delicate and are only for decoration. They don’t stay attached to the cookie when you lift one off the plate.) Place the caramel spider webs on your serving plate, place the chocolate legs where you want the spiders to be, and place the cookies (spider bodies) on top. Place a small dab of melted chocolate on each candy eyeball and place the eyeballs on the cookies.

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