Gingerbread Thumbprint Cookies with Eggnog and Chocolate Filling

Chocolate and Eggnog thumprint cookies

Oh my lanta, the countdown to Christmas has commenced! Unless you start the countdown December first, or in November, then apparently I am way behind the time. But I only just realized that we’ve reached the single digits of days remaining. Eeep! Surprisingly this Christmas I am not feeling particularly overwhelmed. I was better organized with my present purchasing, which made everything go smoothly. Which leaves me with all sorts of time for holiday baking. There has been maximum indulgence this month. I love it!!

Chocolate and Eggnog thumprint cookies

I just realized that I don’t think I’ve ever made thumbprint cookies. And I call myself a baker. Geez. I am not sure how or why I’ve never made them before, but there is a first time for everything! I must say, these were an excellent first choice. Soft and chewy molasses cookies perfectly spiced dolloped with excellent, creamy fillings. I decided to make two separate fillings since there are some non-eggnog lovers in the family (gasp! how dare they!?). I personally thought the eggnog/white chocolate filling was better than the chocolate. But, then again, I am partial to eggnog. These cookies were all gone within a matter of days. Everyone loved the soft cookie (The cooke would be excellent by itself too I think), and creamy fillings. The eggnog and white chocolate was topped with a sprinkling of cinnamon, but nutmeg would also be a great choice. I’m pretty sure Santa would be pretty darn happy if a plate of these were left out for his late night escapades. I’m just sayin’.

Chocolate and Eggnog thumprint cookies
Chocolate and Eggnog thumprint cookies

Gingerbread Thumbprint Cookies with Eggnog and Chocolate Filling

Yield: 36-40 cookies

For the cookies

  • 16 Tablespoons unsalted butter, softened

  • 3/4 cup dark brown sugar, packed

  • 2 large eggs

  • 3/4 cup molasses

  • 1/4 cup real maple syrup

  • 4 1/2 cups all-purpose flour

  • 1 1/2 teaspoons baking soda

  • 1 Tablespoon ground ginger

  • 1 Tablespoon ground cinnamon

  • 3/4 teaspoon ground nutmeg

  • 1/2 teaspoon kosher salt

For rolling

  • 1/4-1/3 cup granulated sugar

For the eggnog filling

  • 1/4 cup eggnog

  • 1 cup white chocolate chips

For the chocolate filling

  • 1/4 cup heavy cream

  • 1 cup semi-sweet chocolate chips


In the bowl of a stand mixer fitted with the paddle attachment, cream together the butter and dark brown sugar until light and fluffy, about 4 minutes on medium-high speed. Mix in the eggs, molasses and maple syrup until combined. Scrape down the sides of the bowl.

In a medium bowl, whisk together the flour, baking soda, ginger, cinnamon, nutmeg and salt. With the mixer on low speed, slowly mix in the flour mixture until no streaks remain and completely combined.

Place the bowl of cookie dough in the refrigerator for 30-45 minutes to chill the dough which helps prevent spreading while baking.

Once chilled, preheat the oven to 350ºF. Line three baking sheets with parchment paper or silpat. Place the 1/4 cup granulated sugar in a small bowl. Scoop the chilled dough into small rounds, about 1 1/2 tablespoon sized. Roll in the granulated sugar and place on the prepared baking sheets, spacing about 2 inches apart. Using a round teaspoon, carefully press an indent in the center of each cookie, going about half way down.

Place in the preheated oven and bake for 16 minutes, or until the cookies are cracking and are just soft. They will harden as they cool, but still be nice and chewy. Press the teaspoon in the center of each cookie again, pressing half way down. Let the cookies cool completely before filling.

Once the cookies are cool, making the fillings. Place the white chocolate chips in a microwave safe bowl. Warm the eggnog in a small measuring cup, then pour over the white chocolate chips. Place in the microwave and heat for 1 1/2 minutes. Stir the mixture until all the chips have melted. Using a small spoon, spoon the filling into half of the cooled cookies centers.

To make the chocolate filling, place the chocolate chips in a microwave safe bowl. Warm the heavy cream in a measuring cup and then pour over the chocolate chips. Microwave on high for 1 minute. Stir until the chocolate has completely melted and is smooth. Spoon the melted chocolate mixture into the centers of the remaining half of cookies.

Let the fillings cool and harden completely. You can speed this process up by placing in the refrigerator. Store in the refrigerator or at room temperature, well covered up to 5 days.

Source: Adapted from Two Cups Flour