Indulgent Gingerbread Latte Whoopie Pies to Eat in One Sitting

Whoopie Pie

We can all thank my sister Laura for introducing me to these whoopie pies. She found it in the December issue of Real Simple magazine and asked me to make it for her. I was unable to make this recipe ahead of time and instead made them on Christmas eve. I would have liked to test the recipe and bring the cookies along but this ended up not being a problem. Whoopie pies taste best the day they’re made and I only had one minor hiccup that I would change for next time. If you haven’t already hit the jump to recipe button at the top, I’ll let you know what that is. So with that, let’s dive in!

A Note about Measurements

For this recipe, I haven’t converted all of the measurements into weight. First, there’s nothing wrong with using cups and teaspoons for your dry and wet ingredients. But, the accuracy you get from measuring your ingredients by weight will yield more consistent results. I maybe see myself making these whoopie pies again next December but probably not before then. And since its a dead heat between Stollen bread and a gingerbread house for my signature holiday bake, I’m going to leave the units for this recipe alone. (Stollen bread recipe is forthcoming, watch Patrick Ryan make it if you can’t wait for me to post.)

Advice on the Dough for your Whoopie Pies

Okay, on to the recipe. Its important to assemble your wet and dry ingredients separately and then add the dry ingredients to the wet. You can use the paddle attachment of a stand mixer if you’re feeling lazy or you can use a spatula. I used a spatula to avoid overmixing the dough. If you do use a stand mixer with the paddle attachment, be careful not to overmix. The dough is going to look kinda “slack” when its first mixed. This is why the chilling time for the dough is important. The chilling time of the dough in the fridge is a minimum of an hour. The dough needs to gets cold enough so that it holds its shape when you put it on the baking tray.

Shaped Dough Balls pre-bake
Baked cookies cooling on a rack.

More Advice on the Dough for your Whoopie Pies

If the dough is too warm going into the oven, the cookies aren’t going to rise properly. This won’t effect the taste of the cookies, they’ll just be closer to little debbie oatmeal creme pies than whoopie pies. They’ll still be delicious, just maybe a bit stodgy. As you can kinda see above, (still working on my food photo skills), the cookies on top got a better rise than the ones on the bottom. Its important to have the dough very cold when its shaped and put in the oven to bake. This will help the dough keep its shape and not flatten out too much when they bake. So make sure the dough is cold so your cookies get that nice fluffy texture.

Advice on the Filling for your Whoopie Pies

For the filling, I’d recommend setting the cream cheese out to warm up for a bit so that it mixes easily. I’d also recommend using an electric mixer for this. Even at room temperature, cream cheese is tough to whip by hand. One mixed and ready to use, its important to have the frosting at the right temperature. The ideal temperature is warm enough to work with but cold enough that it will retain its shape. So if you’re feeling guilty about not getting a forearm workout in when you didn’t mix the frosting by hand, this is your chance for redemption. This is assuming you’re being fancy and piping the frosting and not just smearing it on with a knife. Nothing wrong with that approach either, you do you. Just be ready for your arms to be sore from squeezing the piping bag.

Frosting for your Whoopie Pies if you’re feeling fancy.
Print

Gingerbread Latte Whoopie Pie Recipe

Smooth cream cheese filling between light and fluffy gingerbread cookies make these cookies irresistible.
Course Dessert, Snack
Cuisine American
Keyword Cookies, Fillings
Prep Time 45 minutes
Cook Time 10 minutes
Dough Chill 1 hour
Servings 12 cookies

Equipment

  • Stand Mixer
  • Piping Bag with large frosting tip
  • Wire cooling rack

Ingredients

Cookies

  • 2-1/4 cup all-purpose flour
  • 2 tsp Cinnamon
  • 1 tsp Baking soda
  • 1/2 tsp Baking powder
  • 1/2 tsp Kosher Salt
  • 1/2 tsp Ground Nutmeg
  • 1/2 tsp Ground Cloves
  • 2/3 cup White Sugar
  • 1/2 cup Vegetable oil
  • 1/4 cup Plus 2 tbsp Molasses
  • 1/4 cup Warm water
  • 1 Large Egg room temperature

Whoopie Pie Filling

  • 2 cups Powdered Sugar
  • 6 oz Cream cheese
  • 1/2 stick Unsalted Butter, softened
  • 1/4 tsp Kosher Salt
  • 1 tbsp Espresso Powder
  • 1 tsp Vanilla Extract

Instructions

Cookie Dough Instructions

  • Whisk flour, cinnamon, baking soda, baking powder, salt, nutmeg, and cloves together in a medium bowl and set aside.
  • Whisk the sugar, oil, molasses, water, and egg together in a large bowl until well combined.
  • Fold the flour mixture into the molasses mixture with a spatula until well combined.
  • Cover with plastic wrap and place in the fridge to chill for at least one hour.

Cream Cheese Filling Instructions

  • In the stand mixer with the whisk attachment, combine the powdered sugar, cream cheese, butter, and salt and mix on low speed until smooth.
  • In a separate small bowl, add the espresso powder to the vanilla extract and stir until espresso powder is dissolved.
  • Add espresso vanilla mixture to cream cheese mixture and beat on medium speed until combined and entire mixture is very smooth, around 2 minutes. Cover with plastic wrap in the fridge until ready to use.

Baking and Assembly

  • Preheat oven to 350 deg F with racks in the upper and lower third of the oven.
  • Line two rimmed baking trays with parchment paper
  • Take 1 tablespoon of dough, shape it into a ball and place onto the baking tray, leaving 3 inches between each cookie and the edge. Once tray is ready, put it immediately in the oven in the lower third rack. If left out too long, the cookie won't bake up to be light and fluffy.
  • Bake for 8-10 minutes or until edges of cookies appear to be set.
  • Let cookies cool in the tray for 5 minutes and then transfer to a wire rack to cool completely, around 30 minutes
  • With about 5-10 minutes left in the cooling time, take the cream cheese frosting out of the fridge to warm up so that its easier to pipe.
  • Place the frosting in a piping bag with a large tip and pipe frosting on the flat side of half of the cookies.
  • Top the frosted cookies with the remaining cookies to make sandwiches and enjoy.
  • Cookies can be stored in an airtight container in the fridge for 1 week but they taste best when fresh.
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