For the strawberry cake: Whisk together the flour, baking powder and salt in a medium bowl and set aside. Whisk together the milk, jam and food coloring in a small bowl and set aside. Beat together the sugar, oil, vanilla, vinegar and eggs in a mixer on medium-high speed until pale and smooth, 2 to 3 minutes. In three additions, alternately add the dry and wet ingredients to the sugar mixture, beginning and ending with the dry. Mix until combined.
For the dark chocolate cake: Whisk together the flour, 1/2 cup cocoa, baking soda and salt and set aside. Cream together the sugar and butter. Add the eggs one at a time, creaming well after each addition. Mix in the vanilla extract. Add the flour mix and buttermilk alternately, beginning and ending with the flour.
Mix the strawberry and the chocolate cake batters together. Add the remaining 1/3 cup cocoa and the chocolate pudding mix (this is the red velvet).
For the white cake: Whisk the flours, baking powder, baking soda and salt together into a large bowl. Set aside. In a bowl of an electric mixer fitted with the paddle attachment, beat the butter and shortening on medium speed until creamy, 3 to 4 minutes. Add the sugar and extracts and beat on medium speed until fluffy, about 3 minutes. Scrape down the bowl, add the egg and egg yolk and beat until just combined. Turn the mixer to low. Add the flour mixture, alternating with the ice water, in three separate additions, beginning and ending with the flour mixture. Scrape down the bowl, then mix on low speed for a few more seconds.
To make the whoopie pies: Preheat the oven to 350 degrees F. Line baking sheets with parchment paper.
Take 1 small ice cream scoop of the red velvet batter and place it on parchment paper. Then get a new 1 small ice cream scoop of the peppermint vanilla cake batter and layer it on top of the red velvet. Then using a knife, swirl the batters together by free hand. This creates one half of your whoopie pie.
Bake until they are cooked through, about 12 minutes. When cool, pipe the Peppermint Cream Cheese Icing on one half and then top with another whoopie pie half.
Peppermint Cream Cheese Icing:
With an electric mixer and paddle attachment, cream the butter until smooth. Next, add the cream cheese and beat until fluffy. Next, add the vanilla (with the mixer on low speed) and peppermint extracts. Then, add the confectioners' sugar in small batches until fully incorporated. Mix until there are no lumps of sugar. Add crushed peppermints to the icing. Place the icing in a piping bag and then pipe onto one half of the whoopie pie and top with the second half.
This recipe was provided by a chef, restaurant or culinary professional. It has not been tested for home use.