The woman who coined the phrase, “Nothing tastes as good as being thin feels,” never ate a homemade Whoopie Pie. These came out so amazing that I renamed them “Whoopie Heaven.” They took a long time to make, but it was oh so worth it! My husband calls them the “Mercedes of cookies.” I think they might be the Rolls-Royce.
The chocolate cake batter is pretty standard, but you will want to use an electric mixer for both that and the filling. The filling requires that you make a paste by cooking milk and flour together on the stove, and then cooling it before adding it to the shortening, confectioners’ sugar, and vanilla. This is the secret to the filling. Anything else and it won’t have that authentic texture and flavor of a real whoopie pie.
Because I can never leave a recipe alone when I cook, I made two slight modifications. First, because I am not a huge fan of vegetable shortening (aka Crisco), I used only butter in the chocolate cake batter. And for the same reason, I substituted coconut oil for 2/3 of the shortening in the filling. (I am a huge fan of coconut oil, and use it a lot in cooking now.) If you want your whoopie pies to be nut-free, however, I recommend staying away from it. I also recommend using Hershey’s or another brand of dark, (Dutch) unsweetened cocoa powder. You will find that different brands will render different variations of chocolate taste, so experiment to find the one you like best. Here is a review of 7 brands: I found online. http://food.allwomenstalk.com/best-brands-of-cocoa-that-every-baker-should-use
So as not to keep you on tender-hooks any longer, here is the recipe. It makes 20 large or 24 small pies:
Chocolate cookie batter:
1/2 cup baking cocoa (unsweetened powder)
1/2 cup hot water
1/2 cup soft butter
1 1/2 cups sugar
2 fresh eggs, room temperature
1 tsp. vanilla extract
2 2/3 cups all-purpose flour
1 tsp. baking powder (Calumet)
1 tsp. baking soda (Arm & Hammer)
1/4 tsp. salt
1/2 cup buttermilk (or 1/2 cup milk to which 1/2 Tablespoon lemon juice or vinegar has been added. Note: Wait 5 minutes to give the milk time to curdle.)
Creamy Vanilla Filling:
3 Tablespoons all-purpose flour
1 cup whole milk (or 1/2 and 1/2)
1/2 cup coconut oil
1/4 cup vegetable shortening (Crisco)
1 1/2 cups confectioners’ sugar
2 tsp. vanilla extract
1. In a small bowl, combine cocoa powder and water. Cool for 5 minutes.
2. In a large bowl with electric mixer, cream butter and sugar until light and fluffy. Beat in the eggs one at a time, followed by the vanilla and the cocoa mixture.
3. In another bowl, combine the dry ingredients and add to the creamed mixture alternately with the buttermilk, beating well after each addition.
4. Preheat oven to 350 degrees F.
5. Drop by rounded Tablespoonfuls, 2 inches apart, onto greased baking sheets. (Try to make them as round and as uniform in size as possible. This gets easier with practice.) For best results choose a middle rack in the oven. If the sheets are too close to the bottom of the oven, you risk scorching the cookies.
6. Bake about 10 minutes or until touching one with your finger does not leave an indent. Remove and cool completely on wire racks while you make the filling.
7. In a small, heavy, saucepan, combine the flour and salt. Gradually whisk in the milk until smooth and cook over medium-high heat while stirring constantly, for 5-7 minutes until a thick paste is formed. Remove from heat, cover, and refrigerate until completely cool.
8. In a small bowl with an electric mixer, cream the shortening, coconut oil, confectioners’ sugar, and vanilla until light and fluffy. Add the flour/milk paste and beat for a full 7 minutes until fluffy.
9. Now comes the fun part: with a frosting tool, spread 2 Tablespoons of the creamy filling on half of the cookies and top with the other half. (I find it makes it easier if I match the cookies up by size and shape first before adding frosting). Store between layers of wax paper in the refrigerator.
10. Devour! These taste even better the next day, if you can believe that. So make ahead if baking for company.