Gingerbread Whoopie Pies

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Total Time 45 minutes

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The most incredibly light, airy, and moist gingerbread whoopie pies filled with fluffy cream cheese filling! These cookies are a must-make for the holidays.  

This post is in partnership with Milk Life

Want more ways to enjoy gingerbread this holiday season? You’re sure to also enjoy my Gingerbread Cake, Gingerbread Loaf, and Gingerbread Cupcakes with Cinnamon Cream Cheese Frosting.

close up top view of gingerbread whoopie pies in a vertical row on a cooling rack with the middle one turned on it's side.

My kids are obsessed with trains. Both of them, the boy and the girl. If there is a train show on Netflix, a train toy, book, picture… they will find it and attach themselves to it like frosting on cake. It’s completely darling and I totally feed into it all the time.

We took them on the Heber Valley Polar Express Christmas Train this week and they absolutely lost their minds in awe of it all. You get authentic-looking train tickets and a sweet old man dressed up in conductor garb comes around to punch your ticket after the train gets moving.

The whole experience is modeled after the Polar Express book/movie and it’s adorable, right down to the hot chocolate and cookies and dancing train workers.

a jar of milk with a straw with gingerbread whoopie pies on a cooling rack in the background.

When you reach the “end” you see the North Pole out the train windows and Santa comes aboard the train to sit with each kid and give them a jingle bell. My kids could not have been more enthralled with the whole thing! After two straight days of jingle bell-ing though, I had to hide them, my poor ears couldn’t take it anymore.

I’m all about Christmas traditions and since having our own tiny little kiddos I’ve been excited to start some of our own. Two things I know are going straight onto our holiday list of traditions? The Christmas Train, and these Gingerbread Whoopie Pies.

stacked gingerbread whoopie pies leaning against a jar of milk with a straw with more pies on a cooling rack faded in the background.

These cookies are straight heaven in your mouth. I can’t convey enough how perfect they are. The flavor, the texture…. all of it. The cookies themselves are so light, airy, and moist and not dense at all. Like little gingerbread pillows of goodness.

And the filling is equally as incredible. So fluffy and creamy and rich, but not overpowering. It’s the perfect compliment to the cookies. I don’t care what your favorite brand is, you can’t buy whoopie pies this good at the store. This beats them all.

top view of a pair of hands holding a cooling rack of gingerbread whoopie pies.

Even during the holidays, when we are up to our ears in sweet treats and we indulge at nearly every meal, I try to make sure we are still getting milk into our diets whenever and wherever we can, especially for my kiddos. And nothing goes better with cookies than milk, am I right??

The great thing about milk is that it can be incorporated into our diets in so many ways, including in sweet treats and baked goods like cookies. These whoopie pies call for milk in the cookie batter, the filling, and of course you’ve got to serve them up with a tall glass of straight-up refreshing milk. My little boy gets so excited whenever we add milk to a recipe and yells “mix da milk, mix da milk!”, it’s so darn cute. Farm-fresh real dairy milk is at the heart of our holiday baking and helps me to make sure my kids are getting the nutrients they need to grow up strong.

stacked gingerbread whoopie pies with the top one missing a bite with a jar of milk with a straw and more pies on a cooling rack faded in the background.
Gingerbread Whoopie Pies | lecremedelacrumb.com
4.81 from 62 votes

Gingerbread Whoopie Pies

The most incredibly light, airy, and moist gingerbread whoopie pies filled with fluffy cream cheese filling! These cookies are a must-make for the holidays. 
Prep: 25 minutes
Cook: 20 minutes
0 minutes
Total: 45 minutes
Servings: 24 cookies
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Ingredients 

  • 2 ¼ cups flour
  • ½ teaspoon salt
  • 1 teaspoon baking powder
  • ¼ teaspoon baking soda
  • 1 ½ teaspoons ground ginger
  • 1 teaspoon cinnamon
  • ¼ teaspoon ground cloves
  • ½ cup unsalted butter, softened
  • ¼ cup brown sugar, packed
  • 1 large egg
  • ¾ cup molasses
  • ½ cup milk
  • 1 teaspoon vinegar

Filling

  • ½ cup unsalted butter, softened
  • 2 ounces cream cheese, softened
  • 2 cups powdered sugar
  • ½ teaspoon vanilla extract
  • ¼ teaspoon ground cinnamon, optional
  • 2 cups marshmallow cream
  • 1-3 tablespoons milk, as needed

Instructions 

  • Preheat oven to 375 degrees and lightly grease a baking sheet. In a bowl or liquid measuring cup combine milk and vinegar and set aside.
  • In a medium bowl whisk together flour, salt, baking powder, baking soda, ground ginger, ground cinnamon, and ground cloves. 
  • In a large bowl cream together butter and sugar until light and fluffy. Beat in the egg. 
  • Add dry ingredients to wet ingredients and mix until just combined. Mix in molasses and milk and vinegar mixture. 
  • Use a cookie scoop or tablespoon to drop scoops of cookie dough onto prepared baking sheet. Leave 2 inches between each cookie dough scoop. Bake until cookies are puffy and set, about 10-14 minutes. Repeat with remaining cookie dough and allow cookies to cool completely. 
  • Prepare the filling by creaming together butter and cream cheese until fluffy. Add powdered sugar and mix on high speed for 4-5 minutes. Mix in vanilla, cinnamon, and marshmallow cream. If needed to make a smooth and fluffy consistency, mix in 1-3 tablespoons milk. 
  • Make whoopie pies by spreading filling between two cookies. Serve immediately or store refrigerated in airtight container up to 3 days. Allow to come to room temperature before serving. 

Notes

Store in airtight container in fridge up to three days. 

Nutrition

Calories: 237kcal | Carbohydrates: 39g | Protein: 2g | Fat: 9g | Saturated Fat: 6g | Trans Fat: 1g | Cholesterol: 30mg | Sodium: 163mg | Potassium: 188mg | Fiber: 1g | Sugar: 27g | Vitamin A: 288IU | Vitamin C: 1mg | Calcium: 49mg | Iron: 1mg

Nutrition information is automatically calculated, so should only be used as an approximation.

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Tiffany of Creme de la Crumb in the kitchen

Welcome!

Hey there, I’m Tiffany – chef, photographer, mother, and avid taco eater. I am passionate about turning simple flavors and ingredients into tasty meals the whole family will love, with minimal prep and cleanup so there’s more time to spend eating and enjoying. Stay awhile, and help yourself to a taco or two!

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4.81 from 62 votes (51 ratings without comment)

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29 Comments

  1. Darcy says:

    2 stars
    Taste is great, but mine were bumpy like the texture of an oatmeal cookie. I wouldn’t call what I made a whoopie pie.

  2. Kimberley says:

    5 stars
    I made these the other day and they were delicious. I used store bought buttermilk vs making my own since I had it in my fridge already. I used my large Pampered Chef cookie scoop to divide the dough and ended up with 12 finished Whoopie Pies. I will be trying your Eggnog Whoopie Pie recipe next!

    1. Tiffany says:

      Nice! I’m glad you enjoyed this recipe and hope you enjoy the next one as well 🙂

  3. Victoria says:

    sounds like you need more flour. I always do 1 test cookie first that way you can add more flour this dough should be quit thick – I make the chocolate ones and have a different filling recipe I freeze mine and take out a few at a time

  4. Chris says:

    2 stars
    Not sure why, but my cookies were completely flat, and burned after 10 minutes. I followed the instructions exactly as well. Has anyone else experienced this?

  5. Kim says:

    Can I just use buttermilk instead of milk+vinegar?

  6. Julianne Whitney says:

    Do you use light or dark brown sugar in this recipe?

    1. Tiffany says:

      Light.

  7. Jamie Stretchbery says:

    5 stars
    My sisters and I love gingerbread cookies so these are right up our alley!

  8. maryann says:

    3 stars
    Made these tonight thinking I’d put them in a little holiday gift box for some friends. This was a trial run! Loved the cookie part of this gob (in western PA we call this type of cakey sandwich cookie with creamy filling s gob 😍). So again – cookie part was awesome all around. Nice full well rounded gingerbread flavor with a soft cakey texture. Just the right kind of cookie for a gob! Yay! I’m really struggling with the texture of the filling for this gob. ☹️. It is just too runny, not fluffy enough. A gob (or whoopie pie, if you must…) should have a filling that holds its shape when piled on that soft tender cakey bottom cookie and then sandwiched between the top! Nobody wants a gob whose filling squishes out when you bite into it – let alone squishes out just under the weight of the top part of the cookie!!! It’s super sweet so I didn’t want to add more powdered sugar to try to thicken it. Bottomline: this one won’t make it into the cookie box for my friends…. The cookie is a winner and worth finding the perfect filling for. So I’m on another quest…. Which makes me both happy and sad…. 🙈

  9. Alisha says:

    5 stars
    Just made these and they came out yummy! Thank you for the recipe!

  10. Kriste says:

    5 stars
    Where do you find the milk bottles, I love them and I am trying the gingerbread whoopie pies for thanksgiving! They look amazing

    1. Tiffany says:

      I picked them up at my local home goods store year back, sorry!