Shoo Fly Whoopie Pies

May 22, 2020

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Have you ever had a whoopie pie? If you have, you know exactly what I’m talking about. If not, let me explain. Imagine a hybrid cookie-cake sandwiching a sweet and fluffy icing. Are you sold, yet? If you haven’t had one, you really must –I think it’s a life requirement. There are likely hundreds of flavors to choose from, although the original whoopie is a chocolate “pie” with a light, vanilla filling.

These portable and handheld desserts are said to be created by the Amish, which makes sense, as we live just minutes away from their communities. These desserts can be found at nearly every roadside stand you encounter, plus local grocery stores have even gotten on the bandwagon and have started selling these regional treats. And rightfully so; they are delicious!

One of the flavors we encountered in our travels was a Shoo Fly Whoopie Pie. We’ll save the Shoo Fly Pie discussion for another post, but imagine a soft and sweet molasses cookie sandwiching a super-sweet cream with just a hint of vanilla (and molasses).

Google wasn’t my friend when I tried to locate a recipe to make for my daughter’s birthday. She happens to not like cake, but loves the flavors of a good wet-bottom Shoo Fly Pie. Some recipes called for ginger (ewww!) and others called for “goo” in the center. Uh, nope. I wanted a simple and flavorful whoopie pie, so, using what I had on hand during quarantine, I was forced to come up with a concoction on my own. Surprisingly, the balance of unsulfured molasses (which can be strong) with dark corn syrup created a perfectly balanced pie flavor. (It was also good because I didn’t have enough of either to make up the liquid portion of the recipe!)

Lets just say, the pies were the hit of the day. If you’ve been in pursuit of an excellent shoo fly whoopie pie recipe, please try this one out. It won’t disappoint.

Shoo Fly Whoopie Pie

A handheld version of shoo fly pie., but in a whoopie pie style!

1 cup granulated sugar
1 cup shortening
1/3 cup unsulfured molasses
2/3 cup dark corn syrup
2 large eggs
4 cups all purpose flour
1 tsp baking soda
1 tsp salt
1/2 tsp ground cinnamon
1 tsp vanilla extract

For the filling

3/4 cup shortening
2-3 cups powdered sugar
1 tsp vanilla extract
1 T milk
1 T Turkey Syrup
1/8 tsp salt

For the crumb topping

1/4 cup flour
2 T brown sugar
1 T shortening

For the Pies: Beat the shortening and sugar until it is light and fluffy. Then add the eggs, vanilla, molasses, and corn syrup and beat for another 1-2 minutes, or until your mixture is smooth. Then, add all of your dry ingredients to the bowl and beat on low speed until blended. Your dough will be thick –almost like a cookie dough –that's the way you want it! Cover your dough and place it in the refrigerator for 30-60 minutes. You can do this while you make the filling and crumbs for the recipe.
For the filling: Cream shortening, vanilla, salt, milk, and turkey syrup together. Then add 2 cups of the powdered sugar and beat until light and fluffy. Add up to 1 more cup of powdered sugar to achieve the consistency you'd like.
For the crumb topping: Blend flour, brown sugar, and shortening together using a fork or pastry blender until it has an even consistency.
Baking and assembling: Preheat oven to 350 degrees F. Using a large scoop, make 24 pies (you might have a tablespoon or two of extra dough –that's okay!).
Roll each scoop of molasses-y goodness into a ball, then dip half of them into the crumb mixture (these will be the tops). Place on a lined cookie sheet. You don't want to overcrowd the sheet or else your pies might run into each other –I recommend no more than 6-8 pies on a sheet at at time.
Bake for 10-12 minutes and allow to cool.
Flip over the 12 pie halves that do not have crumbs on them. These are the bases of your pies.
Using the same size scoop as what you used for your pies, load each one of the them with filling. (I find a 2 to 1 ratio of pie to filling best.)
You can adjust this ratio as you'd like, but by using the same size scoop, you achieve this ratio –plus, you don't have people fighting over the pies with the most filling!
Now take the 12 pie halves that have crumbs and place one of each mound of filling. Give it a gentle press so that all of the fluffy goodness oozes to the edges. Wrap in plastic wrap and refrigerate –if they last that long!