I made Whoopie Pies for the very first time last Christmas. Wow, are they good! However, they are a bit of work, and the recipe only makes 16 cookies, so if you’re making these for a cookie exchange, leave yourself a lot of time! The creamy filling is actually an old-fashioned ermine frosting recipe usually found on a Red Velvet cake. Yumm!!
1/2 cup shortening
1 cup sugar
1 teaspoon baking soda
1/8 teaspoon salt
1-1/4 cups buttermilk or sour milk
1 teaspoon vanilla
2-1/4 cups all-purpose flour
2/3 cup unsweetened cocoa powder
Preheat oven to 350° F.
In a large bowl, beat shortening with an electric mixer on medium to high speed for 30 seconds. Add sugar, baking soda, and salt. Beat until combined, scraping bowl occasionally. Beat in buttermilk or sour milk, egg, and vanilla until combined. In a medium bowl, stir together the flour and cocoa powder. Beat in as much of the flour mixture as you can with the mixer. Using a wooden spoon, stir in any remaining flour mixture.
Drop a rounded tablespoonful of dough onto an ungreased cookie sheet. Space cookies about 2-1/2 inches apart.
Bake at 350°F for 10 minutes or until the edges are firm. Cool on cookie sheet for 2 minutes. Transfer cookies to a wire rack; let cool.
Spread the flat sides of half the cookies with a rounded tablespoon of Creamy Filling. Top with the remaining cookies, flat sides down. Store in the refrigerator. Let stand at room temperature for 30 minutes before serving. Makes about 16 sandwich cookies.
Creamy Filling: In a small saucepan, combine 3/4 cup milk and 1/4 cup all-purpose flour. Cook and stir over medium heat until thickened and bubbly. Cook and stir 2 minutes more. Remove from heat; cool. In a large bowl, beat 3/4 cup softened butter with an electric mixer on medium to high speed for 30 seconds. Beat in 2 cups powdered sugar until fluffy. Beat in 1 teaspoon vanilla. Beat cooled milk mixture, one large spoonful at a time, into butter mixture. Beat on high for 1 minute or until filling is smooth and fluffy.