Old-fashioned Whoopie Pies

Instructions

1. 1

   To really bring out the chocolate flavor in these whoopie pies, start by blooming the cocoa. Simply whisk together hot water and cocoa, and set aside for five minutes to cool.

2. 2

   In a large mixing bowl, cream together the shortening and sugar until light and fluffy. This should take five to seven minutes, so don't rush it. Creaming these ingredients properly dissolves the sugar for a smooth batter, and it adds air so you get fluffy whoopie pies (which you want!). Once creamed, add in the eggs, vanilla extract and cocoa mixture, and beat until well blended. Then, in another bowl, whisk together the dry ingredients for the batter: flour, baking powder, baking soda and salt. Add the dry mixture to the wet batter, a little at a time, alternating with the buttermilk. Beat the mixture as you combine everything. The result should be more like cake batter than cookie dough.

3. 3

   Scoop 2 teaspoons of whoopie pie batter using a cookie scoop or spoon, and drop the batter onto a greased cookie sheet or parchment-lined baking sheet. Leave about 2 inches between each cookie because they will spread slightly in the oven. Bake the cookies at 350ºF until they feel firm, 10 to 12 minutes. Then, remove the cookie sheet from the oven, and place the whoopie pies on a wire rack to cool completely.

4. 4

   To make the whoopie pie filling, combine the flour and salt in a saucepan. Gradually whisk in the milk until smooth. Cook over medium-high heat until thickened, five to seven minutes, continuing to whisk as it thickens. Once the filling is thickened, cover it and refrigerate until completely cool. You can even make the filling a day in advance and let it sit in the fridge overnight.

5. 5

   In a bowl, cream together the shortening, confectioners' sugar and vanilla until light and fluffy, three to four minutes. Then, add the cooled milk mixture you made in the previous step, and beat for an additional seven minutes. The end result should be a very fluffy frosting.

6. 6

   All that's left to do is to put the whoopie pies together. Use an offset spatula to cover the flat side of one cookie with some of the frosting, and sandwich it with the flat side of another cookie. Repeat until you've used up all the cookies and frosting—then your homemade whoopie pies!