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Inside-Out Chocolate Cupcakes

This recipe for Inside Out Chocolate Whoopie Cupcakes is the result of my long-standing love of whoopie pies. Whoopie pies have long been one of my favorite treats.  My mom used to spoil my brothers and me by making huge batches of whoopie pies that would be waiting for us after school.   Our family's traditional whoopie pie recipe is made with a filling that cooks together milk, flour, and vegetable shortening.  We are not fans of the fillings that use a marshmallow fluff base.  We're very fussy like that!

Inside-Out Whoopie Cupcakes
Inside-Out Chocolate Whoopie Cupcakes

These chocolate cupcakes have all of the things we love about whoopie pies.  They start with a moist and delicious chocolate cupcake. The chocolate cupcake is filled with the traditional whoopie pie cream filling and then that same cream filling is used as the frosting on top.  You can't get any better than that.  Yummy cream inside and outside!  That's why I call these cupcakes Inside-Out Chocolate Whoopie Cupcakes.

Long gone are the days when I could or would eat two or three whoopie pies after school, but I still love to make desserts that remind me of those days gone by.  I can tell you that without a doubt these cupcakes will make a special treat for those in your life with a sweet tooth.  These cupcakes will also be a hit at your picnics this summer.  Don't worry about the cream filling and frosting.  Cooking the ingredients makes the filling very stable.

Inside-Out Chocolate Whoopie Cupcakes
Inside Out Chocolate Cupcake Ingredients
Very Chocolate Cupcake Ingredients
Printer Friendly Recipe
Makes 20 cupcakes

For the Cupcakes:

  • 3/4 cup unsweetened cocoa powder
  • 1 1/2 cups all-purpose flour
  • 1/1/2 cups granulated sugar
  • 1/1/2 teaspoons baking soda
  • 3/4 teaspoon baking powder
  • 3/4 teaspoon salt
  • 2 large eggs
  • 3/4 cups buttermilk, shaken
  • 6 Tablespoons vegetable oil
  • 3/4 cup warm water
  • 1-teaspoon vanilla

Preheat the oven to 350 degrees F.  Fill the cups of your muffins tins with paper liners.  In a bowl, add the dry ingredients: cocoa, flour, sugar, baking soda, baking powder, salt.  Stir to combine.
With your electric mixer on low (I used my hand mixer for this) stir in the eggs, water, buttermilk, vegetable oil and vanilla until combined.  Mix on medium speed for about 2 minutes until the ingredients are fully combined and the batter is smooth.  For uniform cupcakes, use a scoop to divide the batter into the muffin cups.  Bake for about 20 minutes on the center rack of the oven.  

A pan of baked chocolate cupcakes.
The Cooling Cupcakes

Let cupcakes cool in the pan completely before filling and frosting them.

Whoopie Pie Filling
The Whoopie Pie Cream Filling

For the Filling
  • 1-cup milk
  • 3 Tablespoons flour
  • 1-cup solid shortening
  • 1-cup sugar
  • 1-tsp vanilla


To make the filling: In a saucepan over medium heat, combine the milk and flour.  Cook, stirring constantly until the mixture forms a thick paste. Let cool.
In a medium bowl, beat sugar and shortening until fluffy. Add vanilla. Add cooled flour mixture and beat until double in volume.  The filling will be smooth and creamy.

To Fill and Frost the Cupcakes

Use a pastry bag to squirt the whoopie pie filling into the center of the Very Chocolate Cupcakes.  It is easy to squirt the filling into the top of the cupcake.  You'll be frosting over the top so no one will know how the filling was inserted.
Fill the chocolate cupcakes.
Filling the Cupcakes with Cream Filling
Pipe additional whoopie pie filling on top of the Very Chocolate cupcakes.
A pan of frosted chocolate cupcakes.
Inside Out Chocolate Whoopie Cupcakes
Moist, chocolate cupcakes are always a big hit.  Make them even better with the addition of whoopie pie cream filling and frosting.  So good!

Here are a couple of other cupcake recipes you may enjoy:
Boston Cream Cupcakes
Red Velvet Cupcakes #1

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  1. These look so good!I'll have to save this recipe for later.

    1. Thanks, Brittany. You can get other yummy cupcake recipes from my Cupcake Pinterest board here:

  2. This looks really good. Thank you for sharing it.

    1. Lee, you might like my post for whoopie pies. You can find the recipe here:

  3. My husband is from Northern Maine and for some reason whoopies are a HUGE thing for him and his family. They were completely new to me when I met him! But these cupcakes look like a great new twist on them. Thanks for sharing!!

    1. Tina, my dad grew up in Maine so I know just what you are talking about. Whoopie pies are loved throughout New England, but I think especially in Maine. This cream filling is not too sweet and is traditionally what you will find in a New England whoopie pie.


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