Inverted Cupcakes – [Red Velvet Whoopie Pies]

In February I received a Woopie Pie baking tray (heart shaped) as part of a birthday gift from one of my friends.  I decided to put the tray to the test and bake a Red Velvet Whoopie Pie recipe from my favourite baking book – Butter.  Previous to baking this recipe I had never baked or eaten a Whoopie Pie; however, after baking this recipe, Whoopie Pies have become one of my favourite things to bake and eat!  I think the best way to explain the texture is similar to a cake, yet in the shape of a macaroon with yummy cream cheese butter frosting in the middle.  I was surprised how light and moist these Whoopie Pies turned out.  I definitely will be making these again for a future party!

photo 1 (5)

Inverted Red Velvet Cupcakes


Whoopie Pie
1 cup butter
1/2 cup dark chocolate chips
2 1/2 cups all-purpose flour
1/4 cup dark cocoa
2 teaspoons baking powder
1/2 teaspoon baking soda
1/2 teaspoon salt
1 cup granulated sugar
3/4 cup sour cream
2 large eggs
1 tablespoon white vinegar
1 teaspoon pure vanilla
1 tablespoon red food colouring

Frosting – Cream Cheese Butter Cream
Ingredients below is for 18 cupcakes, so I would half it for the Whoopie Pie as you don’t need that much frosting!
1 1/2 cups butter, room temp
1/2 cup cream cheese, room temp
4 cups icing sugar
1/2 cup whole milk
2 tablespoons pure vanilla

PREHEAT: Oven to 350 F

MELT: butter and chocolate in a small saucepan over low heat, or melt in microwave for ~30 sec.  Set aside to cool

COMBINE: flour, cocoa, baking powder, baking soda and salt.

WHISK: together sugar, sour cream, eggs, vinegar and vanilla to combine.  Add the red food colouring and whisk gently.

COMBINE: melted chocolate to the wet mixture and whisk to combine.  Sprinkle the dry ingredients over the batter and whisk until well combined.

BAKE: use ice cream scoop to drop the batter in 10 equal portions onto the prepared cookie sheets, about 1 1/2 inches apart.  (I also used my heart shaped pre stenciled Whoopie Pie tray).  Bake in preheated oven for 12 – to 15 minutes or until the tops spring back when lightly pressed.

FROSTING: In a stand mixer fitted with a paddle attachment, beat the butter and cream cheese on high speed until very pale in colour.  Scrape down the sides of the bowl at least twice while beating to make sure the butter and cream cheese are evenly combined.  Turn the mixer to low and slowly add the icing sugar.  Mix until well combined then slowly add the milk and vanilla.  Scrape down the sides of the bowl again.  Turn the mixer to high and let it run for at least 10 – 12 minutes. until the butter cream is light and fluffy.

PRESENTATION: remove the cookies from the oven and cool slightly on the cookie sheets, then transfer to wire racks to cool completely.  Turn half of the cookies bottom side up.  Use the piping bag or two spoon to add a heaping tablespoon of butter cream onto each.  Place the remanding cookies on top, right side up, and gently press to sandwich the two together.


2 thoughts on “Inverted Cupcakes – [Red Velvet Whoopie Pies]

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