Not to be confused with my mom’s recipe, these are (literally) pies of a different color – and flavor – thanks to the whole bottle of red food coloring, the buttermilk and the vinegar.
The recipe I used claimed to yield 48 cakes, enough for 24 whoopie pies, but I easily got 60 with my teaspoon batter measure. I will admit that all pies were not quite created quite equal, some batter drops being a bit bigger than others, but let’s consider that a plus – folks can choose the size of their pie(s). I also was able to choose one of the smaller ones when I was, ermm, checking for quality…
Should’ve grabbed a big one – these are GOOD!
One word of warning before we begin – take care working with the food coloring – it can splatter and will stain.
We were planning on painting that wall anyway.
INGREDIENTS
Whoopie Pies:
•3 cups all-purpose flour
•1 tsp baking soda
•1-1/2 tsp baking powder
•2 tsp unsweetened cocoa powder
•1/2 cup canola oil
•1 tsp white vinegar
•1 (1-oz) bottle red food coloring
•1/2 tsp vanilla extract OOPS! I added 1 tbsp – and it was GOOD
•1-1/2 cup sugar
•2 eggs
•1 cup buttermilk*
Frosting:
•8 oz cream cheese, at room temperature
•3 tbsp unsalted butter, at room temperature
•2-1/2 cups confectioners’ sugar, sifted
•1 vanilla bean, halved lengthwise and seeds scraped OR 1 tbsp vanilla extract
*I bought a carton and used the real thing for this recipe, but, if you’re concerned about buying buttermilk and wasting the remainder, check out this recipe for really great chicken. OR, you could make this wicked simple buttermilk substitute.
Preheat the oven to 350º. Lightly grease 2 cookie sheets – I used parchment paper. I should also note that, IMHO, there is no way in HECK you are going to get 24 pies on each cookie sheet – but more about that later…
Sift the flour, baking soda, powder, and cocoa together in a large bowl. In a separate bowl, combine the oil, vinegar, food coloring, and vanilla.
Using an electric mixer, beat the sugar and eggs together in a large bowl until they turn pale and double in volume (this could take a while). Add the oil mixture and beat to combine. Add the flour mixture and buttermilk alternately in 5 small additions, starting and ending with the flour.
Drop the batter by teaspoons onto the baking sheets, allowing 1-inch between drops, as the cookies will spread. I would plan on twelve pies per baking sheet.
Bake until the cakes are firm but not crisp, about 8 to 10 minutes (mine averaged nine minutes).
I baked one sheet at a time – popping the first batch into the oven and then getting the next ready to go while that was baking. This worked out really well for me, since I would 
have otherwise needed five baking sheets for all the batter – as it was, I transferred each baked batch to racks to cool and then set to setting up the next batch. The parchment paper was also a BIG help here, I’m jus’ sayin’.
While the cakes are cooling, you can make the frosting by beating the cream cheese and butter with a mixer until smooth, then beating in the confectioners’ sugar and vanilla seeds (or the vanilla extract).
Sandwich a heaping tablespoonful of filling between 2 pies; repeat with the remaining pies and filling. I eyeballed this measurement based on the size of each pie, but there did seem to be ample frosting to well and truly fill each one.
Refrigerate 30 minutes before serving.