A Different Kind of Whoopie Pie

Old Fashioned Apple Streusel Whoopie Pies

With the crunch of streusel, the fresh taste of apple and the overall ooze of the filling and melted caramel will have you thinking you are biting into an apple pie. I guess you are in a way, an Apple Whoopie Pie. Enjoy these everyone, but kids did!

1 large apple, cored, peeled and wedged into 20 segments
1 c. brown sugar
1/2 c. granulated sugar
1/2 c. butter or margarine, divided
2 eggs
1/2 c. vegetable oil
2 T. vanilla
3 c. flour
2 t. baking powder
1 t.. baking soda
1 t. cinnamon
1/2 t. nutmeg
1/2 t. ground cloves
1 3/4 c. milk
Filling, recipe follows
Streusel topping, recipe follows
30 caramel candies, unwrapped

Preheat oven to 350- degrees F. Either line a baking sheet with parchment paper or liberally oil pan(or use nonstick cooking spray), adding flour enough to lightly coat the oiled pan. Over medium high heat in a large skillet, place the brown sugar and 2 T. butter. Cook one minute or until sugar has melted. Add the apples and caramelize until apples  begin to soften, about 8 minutes covered;set aside.

In a large bowl of an electric mixer, beat the granulated sugar, remainder of butter, and eggs together until well combined. Add the oil and vanilla and beat again. Don’t worry if it looks as though the butter isn’t incorporating very well. Smooth emulsification is nearly impossible here so just beat well.

In a separate bowl, combine all the rest of the dry ingredients. Add the dry mixture to the egg mixture and beat or stir to blend. Add 1 c. milk and beat again. Add caramelized apples and blend until well incorporated. Add the remainder of milk until the mixture resembles very thick batter. You may not need all of it.
With an ice cream scoop or a 1/3 c. measuring cup, dollop batter onto prepared baking sheet, giving each mound a 3-inch space between. Use a spoon to “mold” each mound into a circle shape. Sprinkle about a tablespoon of Streusel Topping over each. Bake for 10 to 12 minutes or until when lightly touched in the center, it springs back. Remove from oven and let cook 1 minute before transferring to a rack or platter to cool.. Let cool.
While cooling make the filling and melt the caramels in the microwave with 1/4 c. milk until melted. Remove from microwave and mix well.

Filling:

1 c. shortening
2 c. powdered sugar
1 c. marshmallow topping
30 caramel candies, melted in microwave
1/4 c. milk

In the bowl of an electric mixer, combine all ingredients except the milk and beat well. Add just enough milk to achieve a creamy consistency. Spread filling across cooled cookie circles.

Streusel topping:
1/2 c. flour
1/2 c. brown sugar
2 T. butter or margarine, melted

When ready to assemble, dollop a hefty tablespoon of the filling on one half of the whoopie pie, Make a well and drizzle some of the melted caramel into this well. Close whoopie Pie and repeat with remainder of whoopie pies. Refrigerate for at least one hour then you can take out and leave them covered on the counter for everyone to enjoy. The purpose of cooling them in the refrigerator is to harden the caramel somewhat so it doesn’t ooze out and begin melting the filling as well.