Homemade Decadent Holiday Gingerbread Whoopie Pies

Add these soft, cake-like, sweet yet spicy, gingerbread whoopie pies as a sandwich-like cookie with decadent cream cheese filling to your holiday baking list this year!

Holidays are all about traditions. Traditions are the glue that spans generations, creates family identity, and makes those family memories that you look back on fondly. One tradition that I’ve had since I was a little girl is making Christmas cookies.

Unfortunately, making Christmas cookies seems to be a dying art, which makes me sad because I have SO many good memories with my sister, my mom, and my grandma making (and eating!) holiday cookies.

Let’s be baking friends! Grab our Christmas cookies mini-cookbook with delicious tried & true recipes we use (and LOVE) year after year.

Growing up in the South, whoopie pies were (and probably still are) a staple. Instead of making the commonplace chocolate and vanilla varieties, though, I wanted to get a little more creative – and festive – for the holidays.

Enter: Gingerbread Whoopie Pies!

These cookies are like little bites of heaven in your mouth. I know it sounds over the top, but they seriously come together in a perfect cacophony of flavors and texture.

Perfectly spiced cake-like gingerbread cookies and creamy, rich cream cheese filling. Alone, each of these parts is delicious.

Together? Look Out! These whoopie pies are so addictive that you’ll need to claim yours before someone else does…and they will. Quickly.

This incredible, rich, and creamy filling is sandwiched between 2 moist, airy, flavor-packed cookies for a sweet and spicy cookie treat.

You can’t find whoopie pies like this is any store. This homemade version is better than ALL of them – combined.

Gingerbread Whoopie Pie Ingredients

Here are the ins and outs regarding the ingredients in this recipe.

Cupcake Ingredients:

• All-purpose flour – the base of this recipe.
• Baking soda & baking powder – gives rise to the mixture.
• Allspice & ground ginger – spices add flavor
• Salt – balances out the sweet and enhances the other flavors
• Softened butter – adds rich flavor and moisture
• Light brown sugar – sweetens and adds a slight caramel flavor
• Buttermilk – adds moisture and the acid needed to react with baking soda to make the dough rise
• Molasses – adds a deeper flavor that complements the ginger
• Egg – binds all the ingredients together
• Holiday sprinkles, if desired – they just make the cookies even more fun!

Frosting Ingredients

• Room temperature unsalted butter – adds rich flavor and creamy texture
• Confectioner’s sugar – sweetens the recipe without adding a grainy texture
• Room temperature cream cheese – creamy base of this recipe
• Half and half – keeps the recipe from being too thick
• Allspice – adds flavor to the frosting

How to Make Christmas Whoopie Pies

Follow these step-by-step instructions and before you know it, you’ll be enjoying eating your homemade gingerbread whoopie pies!

Cookie Directions

Preheat your oven to 350 degrees.

Step 1: In a mixing bowl, add flour, baking soda, baking powder, salt, and ginger. Whisk dry ingredients together.

Step 2: In a small bowl, cream together the brown sugar and butter until light and fluffy. Mix in your egg.

Step 3: Mix in the buttermilk and molasses. Once incorporated, slowly mix in the dry ingredients.

Step 4: Line a baking pan with parchment paper or a silicone baking mat.

Step 5: Using a spoon or ice cream scoop, drop 1” balls onto your baking pan. Bake for 10-12 minutes or until they spring back when pressed lightly with your fingertip. Cool on a wire baking rack.

Frosting Filling Directions

Step 1: Beat cream cheese and butter for 1 minute or until light and fluffy.

Step 2: Add half of the creamer and slowly add in the confectioners’ sugar, 1/2 cup at a time until light and fluffy. If the mixture is too thick, add more creamer, 1 tablespoon at a time.

Step 3: Add allspice and incorporate completely.  

Step 4: Pipe or spoon filling onto a whoopie cookie and top with a second cookie.

Now you have a whoopie pie! If desired, roll in holiday sprinkles.

What Filling Goes With Gingerbread Whoopie Pies

This cream cheese filling is divine with the gingerbread cookies. Another option would be to replace the cream cheese with marshmallow creme for a marshmallow-flavored filling!

That’s not too much work, right? It’s slightly more than say a regular cookie but in the end, you get 2 cookies in every bite with the most heavenly cream cheese frosting in the middle. I’d say it’s completely worth it!

Now that I’ve discovered how to make our own gingerbread whoopie pies, I’m not sure I’ll ever look at non-sandwich cookies the say way again. These are WAY better than non-sandwich, non-frosted cookies!

Let’s be baking friends! Grab our Christmas cookies mini-cookbook with delicious tried & true recipes we use (and LOVE) year after year.

More Holiday Goodies You’ll Love:

• Festive Easy Peppermint Bark Recipe (Only 3 Ingredients)!
• These Easy Pumpkin Pie Bars are incredible!
• Easy Pecan Pie Bars