Gingerbread Whoopie Pies

Mega soft and chewy Whoopie Pies made festive with gingerbread!

This Whoopie Pie recipe takes two tender cake-like gingerbread cookies and sandwiches them with with luscious cream cheese frosting to create your new favorite way to devour gingerbread!  And bonus, you get two Christmas cookies in one!   Make ahead and freezer instructions included!

easy Whoopie Pies recipe stacked on a plate

Whoopie Pie

Can you guys believe Christmas is SO soon?!  I had a gazillion holiday recipe ideas to share with you but there just isn’t enough time so I am only sharing the best of the best like these epic Gingerbread Whoopie Pies that are sure to fill your hearts and bellies with holiday cheer!

I don’t make a lot of cookies, so if I’m going to make them, they have to be worth my time.  And these Gingerbread Whoopie Pies are SO worth my/your time!  This whoopie pie recipe is adapted from America’s Test Kitchen Magazine Christmas Cookies Issue and as I was flipping through, these immediately caught my eye because a) gingerbread,  b) cream cheese filling, c) whoopie pies!!!

I love whoopie pies.  It’s like two reverse frosted cake-like cookies back to back so you get two cookies in one with just the right amount of filling oozing with each bite….but…….that would only be a good thing if you loved the cookies, so let me assure you – you will love these cookies.  

WHY WHOOPIE PIES ARE THE BEST:

  • Festive and delicious
  • MEGA soft and chewy
  • GINGERBREAD
  • That cream cheese filling!
  • Double the cookie!
  • Perfect for a holiday party or family dinner
  • Make ahead friendly

What are Whoopie Pies?

I took the concept for this whoopie pie recipe from traditional whoopie pies that are made of two round mound-shaped pieces of chocolate cake (a cross between cake batter and cookie dough) with a sweet, creamy filling or frosting sandwiched between them.  Traditional filling used to always be a form of sweet marshmallow cream but it has evolved to include buttercream as well.  

Whoopie Pies Recipe

This Gingerbread Whoopie Pie recipe also begins with two round mound shaped cake-like cookies but instead of chocolate, they are gingerbread, and instead of marshmallow filling, we have cream cheese butter cream.

The resulting Whoopie Pies are some of the softest cookies I have ever sunken my teeth into and the cinnamon, ground ginger, crystallized ginger, nutmeg, and cloves add a festive complexity of flavor that compliments the silky sweet cream cheese filling.   They will make you merry – for days.

the best whoopie pies recipe stacked on a pate

Why do they Call it a Whoopie Pie?

I love this story!  Whoopie Pies originated in New England as a Pennsylvania Amish tradition.  They were often made with leftover cake batter so they were considered a special treat.  According to Amish legend, children would exclaim, “whoopie!” when they  discovered the pies in their lunch bags. 

What is Whoopie Pie Filling Made of?

This  Whoopie Pie filling skips the marshmallow fluff and instead uses more of a frosting-like filling reminiscent of frosting gingerbread.  The Cream Cheese filling is a buttery blend of sugar, butter, cream cheese and vanilla for a luscious, silky filling that will have you licking the beaters.  

You can pipe the filling onto half the cookies or you can simply drop it by the tablespoon and then top with the remaining cookies for adorably petite, zesty Gingerbread Whoopie Pies bursting with molasses, cinnamon and spices.  Bursting with holiday cheer!

showing how to make Whoopie Pies by filling with whoppie pie filling without fluff

HOW TO MAKE Whoopie Pie Recipe

Making the Batter

  • Don’t skip the crystallized Ginger.  This Whoopie Pie recipe calls for crystallized ginger.  You do NOT want to skip this!  I made two batches of Gingerbread Whoopie Pies – one without crystallized ginger and upping the ground ginger and one with the crystallized ginger.  The batch with just ginger powder tasted flat and bland while the batch with crystallized ginger boasted a sweet bite that complimented the sweetness of the filling.  In short, adding crystallized ginger is the only way for these cookies to live up to their name “Gingerbread!”
  • DIY Buttermilk.  Don’t have buttermilk? No problem, you can still make these Whoopie Pies!  Simply add one teaspoon lemon juice or vinegar to a measuring cup then add enough milk to equal ¼ cup and give it a stir.  Let it sit for 5-10 minutes.  When it curdles on top, you know it’s ready to use. 
  • Refrigerate dough.  I know refrigerating dough can be a pain because we all want whoopie pies NOW, but you will need to refrigerator the dough for at least 1 hour up to 24 hours.  This will not only develop the festive flavors but will prevent your dough from spreading out too much when it bakes, maintaining that “mound” shape we know and love. 

Baking the Whoopie Pies

  • Line baking sheets.  You will need to line your baking pans with either parchment paper or nonstick mats.  I don’t recommend foil with cooking spray because this will make your dough spread out too much.
  • Don’t overbake pies.  Bake pies just until puffed and just set, 11-13 minutes.  The pies will continue to cook as they cool, so it is important not to over bake them for the SOFTEST whoopie pies around. Better to underbake than overbake in my opinion.

Making the Filling

  • Use paddle attachment.  If you have the paddle attachment for your mixer, this is optional for the the fluffiest frosting.   Make sure you beat your butter and sugar for a full two minutes so the frosting will whip in tons of air and become super fluffy. 
  • Refrigerate frosting to thicken.  If your filling is very soft, then refrigerate it for 15 minutes before filling cookies (I didn’t have to do this). This can often result when butter or cream cheese that is too soft to begin with.  Take care to NEVER microwave your butter for frosting or it can easily become too soft. 

Filling Whoopie Pies

  • Assemble.  Spoon or pipe 1 tablespoon frosting evenly onto bottoms (flat sides) of 24 cookies. Top with remaining 24 cookies, bottom sides down. Dust with powdered sugar. 
showing how to make Whoopie Pies by adding cookie on top of filling

Can I Make Whoopie Pies Ahead of Time?

Yes!  You can prepare the batter, cover it tightly with plastic wrap and refrigerate for up to three days.  You can also make the cookies a day ahead of filling and keep in an airtight container until ready to fill.  Lastly, you can also freeze the whoopie pies (instructions below).

HOW DO I STORE WHOOPIE PIES?

  Store Whoopie Pies in an airtight container in the refrigerator. Bring to room temperature before serving.  I like to microwave mine for 10 seconds or so.   

CAN WHOOPIE PIES BE FROZEN?

Yes! You can either freeze the whoopie pie battere the baked whoopie pies or the assembled whoopie pies. Here’s how to freeze all three options:

HOW TO FREEZE WHOOPIE PIE DOUGH:

  • Roll balls per instructions and fit as many as you can on a parchment/nonstick lined baking sheet without touching.
  • Place the baking sheet in the freezer and freeze the balls until  outsides are hard (about 1-2 hours).
  • Transfer to a freezer size plastic bag and freeze.
  • Dough should freeze well for up to 3 months.
  • To BAKE:  Place frozen cookie dough balls on a lined baking sheet and bake according to instructions, adding a couple extra minutes to cook time.

HOW TO FREEZE BAKED WHOOPIE PIES WITHOUT FILLING

  • Fit as many COOLED baked whoopie pies on a parchment/nonstick mat lined baking sheet without touching.
  • Place the baking sheet(s) in the freezer and freeze until  solid (about 1 hour).
  • Transfer to a freezer size plastic bag and freeze for up to 3 months.
  • When ready to use, let whoopie pies defrost on the counter before filling.
up close of Gingerbread Whoopie Pies with filling

HOW TO FREEZE ASSEMBLED WHOOPIE PIES

  • Fit as many whoopie pies on a parchment/nonstick mat lined baking sheet without touching.
  • Place the baking sheet(s) in the freezer and freeze until  solid (about 1 hour).
  • You can now freeze individual whoopie pies by placing them each in individual sandwich bags, OR to freeze a batch of pies:
  • Top frozen whoopie pies on baking sheet with a layer of parchment paper and layer with another layer of frozen pies (that you have frozen on a separate sheet).  Continue to layer and stack as needed.
  • Wrap entire baking sheet securely in layers of plastic wrap.
  • To THAW TRAY:  Take baking sheet out of refrigerator and unwrap so that the condensation doesn’t form and make the whoopie pies soggy.  Let sit at room temperature for several hours.
  • TO THAW INDIVIDUAL WHOOPIE PIES:  Take whoopie pie out of the sandwich bag and let sit at room temperature overnight OR if you’re in a hurry,  warm whoopie pie in the microwave at 10 second intervals until defrosted.

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soft Whoopie Pie with a bite taken out of it

 

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©Carlsbad Cravings by CarlsbadCravings.com

Gingerbread Whoopie Pies - everyone always begs me for this recipe! Super soft gingerbread cookies stuffed with luscious cream cheese filling! You won't be able to have just one!

Gingerbread Whoopie Pies

Mega soft and chewy Gingerbread Whoopie Pies stuffed with luscious cream cheese frosting will be your new favorite way to devour gingerbread!  And bonus, you get two Christmas cookies in one!
Servings: 24 pies
Prep Time: 35 minutes
Cook Time: 26 minutes

Ingredients

Cookies

  • 2 cups all-purpose flour
  • 2 teaspoons ground cinnamon
  • 1/2 tsp EACH ground ginger, nutmeg, salt
  • 1/4 teaspoon ground cloves
  • 3/4 teaspoon baking soda
  • 3/4 cup packed light brown sugar
  • 8 tablespoon unsalted butter, melted
  • 1/4 cup molasses
  • 3 tablespoons crystallized ginger, finely chopped
  • 1 large egg
  • 1/4 cup buttermilk
  • 1 teaspoon vanilla extract

Cream Cheese Filling

  • 6 tablespoons unsalted butter, room temperature
  • 1 1/2 cups Powdered sugar
  • 6 oz. cream cheese, cut into 6-8 pieces, softened
  • 1/2 teaspoon vanilla extract
  • Pinch of salt

Garnish (a must!)

  • Powdered sugar for dusting

Instructions

  • Whisk flour, cinnamon, ground ginger, nutmeg, salt, cloves and baking soda together in a medium bowl. Set aside.
  • Whisk brown sugar, melted butter, molasses and crystallized ginger in separate large bowl until combined. Whisk in egg, buttermilk and vanilla until combined. Add flour mixture and stir with rubber spatula just until dough comes together. Cover bowl with plastic wrap and refrigerate for at least 1 hour up to 24.
  • Preheat oven to 350 degrees F. Line 2 baking sheets with parchment paper or nonstick mat. Roll dough into balls using 1 scant tablespoon. Space balls evenly on prepared sheets, about 2 inches apart. Bake cookies, 1 sheet at a time, until puffed and just set, 11-13 minutes. Let cookies cool on sheet for 5 minutes then transfer to wire rack to cool completely before frosting.
  • Using stand mixer fitted with paddle attachment, beat butter and powdered sugar on medium-high speed until fluffy, about 2 minutes. With mixer running, add cream cheese, 1 piece at a time, and continue to beat until smooth, about 30 seconds. Beat in vanilla extract and pinch of salt as needed.
  • *Spoon or pipe 1 tablespoon frosting evenly onto bottoms (flat sides) of 24 cookies. Top with remaining 24 cookies, bottom sides down. Dust with powdered sugar. (Note, these cookies need the dusting of powdered sugar or they won’t taste sweet enough).
  • Store cookies in an airtight container in the refrigerator. Bring to room temperature before serving.

Notes

*If frosting is very soft, refrigerate for 15 minutes before filling cookies (I didn’t have to do this).

MAKE AHEAD: 

You can prepare the batter, cover it tightly with plastic wrap and refrigerate for up to three days.  You can also make the cookies a day ahead of filling and keep in an airtight container until ready to fill.

STORAGE:

Store Whoopie Pies in an airtight container in the refrigerator. Bring to room temperature before serving.  I like to microwave mine for 10 seconds or so. 

HOW TO FREEZE WHOOPIE PIE DOUGH:

  • Roll balls per instructions and fit as many as you can on a parchment/nonstick lined baking sheet without touching.
  • Place the baking sheet in the freezer and freeze the balls until  outsides are hard (about 1-2 hours).
  • Transfer to a freezer size plastic bag and freeze.
  • Dough should freeze well for up to 3 months.
  • To BAKE:  Place frozen cookie dough balls on a lined baking sheet and bake according to instructions, adding a couple extra minutes to cook time.

HOW TO FREEZE BAKED WHOOPIE PIES WITHOUT FILLING

  • Fit as many COOLED baked whoopie pies on a parchment/nonstick mat lined baking sheet without touching.
  • Place the baking sheet(s) in the freezer and freeze until  solid (about 1 hour).
  • Transfer to a freezer size plastic bag and freeze for up to 3 months.
  • When ready to use, let whoopie pies defrost on the counter before filling.

HOW TO FREEZE ASSEMBLED WHOOPIE PIES

  • Fit as many whoopie pies on a parchment/nonstick mat lined baking sheet without touching.
  • Place the baking sheet(s) in the freezer and freeze until  solid (about 1 hour).
  • You can now freeze individual whoopie pies by placing them each in individual sandwich bags, OR to freeze a batch of pies:
  • Top frozen whoopie pies on baking sheet with a layer of parchment paper and layer with another layer of frozen pies (that you have frozen on a separate sheet).  Continue to layer and stack as needed.
  • Wrap entire baking sheet securely in layers of plastic wrap.
  • To THAW TRAY:  Take baking sheet out of refrigerator and unwrap so that the condensation doesn’t form and make the whoopie pies soggy.  Let sit at room temperature for several hours.
  • TO THAW INDIVIDUAL WHOOPIE PIES:  Take whoopie pie out of the sandwich bag and let sit at room temperature overnight OR if you're in a hurry,  warm whoopie pie in the microwave at 10 second intervals until defrosted.

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©Recipe adapted from America’s Test Kitchen Magazine: Christmas Cookies, Gingerbread Whoopie Pies, pg. 55

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46 Comments

  1. Marie says

    I’ve made these twice now and they taste fabulous! My only problem is they get so flat. I would love for them to look like your pictures, fluffy and more cake-like. The first batch, I refrigerated the dough for only an hour. The second batch, I refrigerated the dough overnight. Both times they came out flat. What am I doing wrong?

    • Jen says

      Hi Marie, I would try rolling the dough into balls and then refrigerating. This way the dough doesn’t warm up while you form them. Also, try rolling the dough balls tall – more like an egg -verse perfectly round. Lastly, take care to not stir more than you have to. I hope this helps!

    • Nancy says

      I noticed the recipe doesn’t call for baking powder. Baking powder will give it the rise you need. I made pumpkin whoopie pies and I added both baking powder and baking soda. They came out with perfect little mounds. Hope this helps.

      • Jen says

        Hi Nancy, the recipe uses baking soda instead because it interacts with the buttermilk. enjoy!

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