These Gingerbread Whoopie Pies feature a cream cheese frosting sandwiched between two large, thick, and chewy gingerbread cookies. These cookies are the perfect holiday treat!

A stack of 3 gingerbread whoopie pies.

I’m so glad it’s gingerbread season! I love all things Christmas and holiday related.

This year I’m planning on making: cut out gingerbread cookies, gingerbread bundt cake, soft gingersnap cookies, and of course the best sugar cookies ever!

Adding to that list will be these soft gingerbread cookie sandwiches.

Now, let me tell you a few things I really enjoy about these cookies:

  1. These are definitely gingerbread cookies, however, they aren’t so incredibly overloaded with molasses and ginger that you gag and wish you had a gallon of milk to chug. Truth be told, I don’t love overly strong molasses flavors. If you’re like me you’ll go crazy for these cookies. Like, 1000% crazy for them.
  2. They’re soft and thick and so chewy.
  3. The cream cheese filling is luscious and smooth and seriously spot on!
  4. Technically you eat 2 cookies when in actuality you’re eating just 1 (whoopie pie). Woohoo!

A row of gingerbread whoopie pies.

How to make Gingerbread Whoopie Pies

Prep the Baking Sheets

Begin by lining two baking sheets with parchment paper or a silicone baking mat. If you’re not using mats or parchment, spray the cookie sheets with cooking spray.

Mix the ingredients

In a large bowl, or the bowl of a stand mixer fitted with the paddle attachment, cream the butter and brown sugar on medium speed for 2 minutes or until fluffy.

Add the molasses and the eggs, one at a time, mixing well after each addition.

Mix in the baking soda, ginger, cinnamon, salt, cloves, and flour. Don’t over mix the dough as this will result in a tough and dense cookie.

Gingerbread Whoopie Pie dough in a glass bowl.

Portion the dough

Scoop the soft dough into 24 — 1 3/4″ inch balls. Roll each ball in granulated or coarse sugar.

Place the balls on the baking sheet about 2 inches apart from one another.

Pro tip: I placed 6 cookies on each baking sheet to avoid any chance of the cookies baking into one another

Gingerbread cookie dough balls rolled in granulated sugar.

Bake the Cookies

Bake the cookies for 9-11 minutes or until the edges re set and lightly golden brown.

Cool the cookies on the cookie sheet for 2-3 minutes and then transfer the cookies to a cooling rack to cool completely.

Baked gingerbread cookies.

Make the filling

To make the filling beat the cream cheese until smooth. Once smooth add the powdered sugar and vanilla and beat until smooth.

How to assemble the whoopie pies

To assemble the whoopsie pies, spread or pipe the filling the flat sides of half of the cookies.

Gently press the flat sides of the remaining cookies against the filling. Chill the whoopie pies to help the filling set.

Store in the fridge for 2-3 days.

These gingerbread whoopie pies are soft, chewy, thick, and have amazing flavor! Make them and you’ll LOVE ’em!

A bite taken out of a Gingerbread Whoopie Pie.

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Gingerbread Whoopie Pies

The BEST gingerbread cookies you'll ever have! Smooth cream cheese frosting is sandwiched between two soft gingerbread cookies resulting in delicious gingerbread whoopie pies.
prep time 25 mins
cook time 10 mins
total time 35 mins
servings: 12 whoopie pies
calories: 579kcal

INGREDIENTS

Gingerbread Cookies

  • 1 cup butter softened to room temperature
  • 1 1/4 cup brown sugar packed
  • 1/3 cup molasses
  • 2 teaspoons baking soda
  • 1 teaspoon ground ginger
  • 1 teaspoon ground cinnamon
  • 1/2 teaspoon salt
  • 1/2 teaspoon ground cloves
  • 2 large eggs at room temperature
  • 4 cups all purpose flour
  • granulated or coarse sugar

Cream Cheese Filling

  • 8 oz cream cheese softened
  • 2 1/2 cups powdered sugar
  • 1 teaspoon vanilla extract

INSTRUCTIONS

Gingerbread Cookies

  • Preheat oven to 350°F. Line two baking sheets with parchment paper or silicone baking mats. If not using mats, spray the cookie sheets with cooking spray. 
  • In the bowl of a stand mixer fitted with the paddle attachment, or using hand beaters, beat the butter and brown sugar on medium speed for 2 minutes or until fluffy. Add the molasses and mix until combined. Add the eggs, one at a time, mixing well after each addition. 
  • Add the baking soda, ginger, cinnamon, salt, and cloves and flour. Mix until combined. 
  • Scoop the soft dough into 24 - 1 ¾" inch balls. Roll each ball in granulated or coarse sugar. Place the balls on the baking sheet about 2 inches apart from one another. 
  • Bake for 9-11 minutes or until the edges are set and lightly golden brown. Cool the cookies on the cookie sheet for 2-3 minutes and then transfer the cookies to a cooling rack to cool completely. 

Cream Cheese Filling

  • In a medium bowl beat the cream cheese until smooth. Add the powdered sugar and vanilla and beat until smooth. 

Assemble the Whoopie Pies

  • To make the whoopie pies spread or pipe the filling on the flat sides of half of the cookies. Gently Press the flat sides of the remaining cookies against the filling. Chill the whoopie pies to help the filling set. Store in the fridge for 2-3 days. 

RECIPE NOTES

Nutritional info is based on 1 whoopie pie.
Calories: 579kcal | Carbohydrates: 87g | Protein: 7g | Fat: 23g | Saturated Fat: 14g | Cholesterol: 97mg | Sodium: 500mg | Potassium: 256mg | Fiber: 1g | Sugar: 55g | Vitamin A: 778IU | Calcium: 74mg | Iron: 3mg
Course: Dessert
Cuisine: American
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