SMiLes by Meg

Chocolate Whoopie Pies

Full disclosure: I made these on the 3rd of July, not the 3rd of August.  But as I mentioned earlier, when you don’t have a staff room to drop the treats off in on Monday morning, you have to save some recipes for later if you want to save yourself from death by diabetic coma.

Anyways, I made them for the third of July because I wanted to make something that seemed like a good, wholesome American dessert without being explicitly red, white and blue.  I also wanted to make something on the smaller side that could be enjoyed in addition to lots of other yummy cookout food.  That led me to set out to find a good whoopie pie recipe.

Shockingly, just regular chocolate cookie/vanilla filling whoopie pie recipes were hard to come by. I was under the impression that that was the standard combination, but apparently the variations have taken over.

However, I knew I needed the original. One Thanksgiving, I made the grave error of going with pumpkin whoopie pies with cream cheese filling.  My dad declared them an abomination of the whoopie pie, which was actually the same way I felt about my mom’s gingerbread version of the chocolate trifle – apparently there are some recipes that really should not be seasonally modified.

Anyways, unwilling to again endure the wrath of my father by going with the seemingly more popular mint chocolate version, here is your standard, chocolate and vanilla whoopie pie.

First, beat the sugar and oil together until crumbly.  This is fine to use a hand mixer for, I just didn’t have one on hand.

Chocolate Whoopie Pies - 1Chocolate Whoopie Pies - 2

Next, add the eggs and beat well.

Chocolate Whoopie Pies - 3

Chocolate Whoopie Pies - 4

In a separate bowl, whisk together the flour, cocoa powder, and baking soda.

Chocolate Whoopie Pies - 5Chocolate Whoopie Pies - 6Gradually beat the cocoa mixture into the egg mixture.  I usually add about a third at a time and beat until combined.

Chocolate Whoopie Pies - 7Chocolate Whoopie Pies - 8Chocolate Whoopie Pies - 9Add the milk and beat well.  Though not as pretty as my yellow one, my mom’s red stand mixer does get the job done.

Chocolate Whoopie Pies - 10Chocolate Whoopie Pies - 11This dough is really sticky, so it takes a bit of flour to really handle it.  Spray a cookie sheet with cooking spray and lightly (or heavily) flour your hands.  Roll dough into about 1 inch balls (or bigger, but I wanted two-bite treats) and place two inches apart on the cookie sheet.  Spray the bottom of a glass with cooking spray and flatten the top of each ball slightly.

Chocolate Whoopie Pies - 12Bake at 425°F for 5-6 minutes.  Tops should crack before you remove them from the oven, after which you should let them cool on the cookie sheet for 3 minutes before transferring to a wire rack to cool completely.

Chocolate Whoopie Pies - 13Chocolate Whoopie Pies - 14While those are cooling, you can make the filling.  First, beat together the shortening and confectioner’s sugar.

Chocolate Whoopie Pies - 15While beating, add the milk and vanilla extract and beat until fluffy.  Scrape down the sides at some point to ensure all of that sugary goodness is going into it.

Chocolate Whoopie Pies - 16Chocolate Whoopie Pies - 17Chocolate Whoopie Pies - 18Once you are SURE that the cookies are cool, you can spread a little of the filling on the flat side and top with the flat side of a second cookie, like so:

Chocolate Whoopie Pies - 19Chocolate Whoopie Pies - 20Look how little they are!  Anyways, serve same day if you want the filling to still be soft – otherwise you run the risk of hard frosting.  Not a bad thing, but not quite as appealing to the masses.


Chocolate Whoopie Pies - 21

Chocolate Whoopie Pies

Cookie Ingredients:

  •  1 cup sugar
  • 6 tablespoons vegetable oil
  • 2 eggs
  • 2 cups all-purpose flour
  • 1/2 cup cocoa powder
  • 1 teaspoon baking soda
  • 4 tablespoons milk

Filling Ingredients:

  • 4 tablespoons shortening
  • 3 to 3 1/4 cups confectioners’ sugar
  • 4 tablespoons milk
  • 1/4 teaspoon vanilla extract

Cookie Directions:

  1. Beat together sugar and oil until crumbly.
  2. Add eggs and beat well.
  3. In a separate bowl, whisk together flour, cocoa powder, and baking soda.
  4. Add chocolate mixture to egg mixture gradually, beating well.
  5. Add milk and beat well.
  6. Flour hands and roll dough into 1 inch balls.  Place on cookie sheet sprayed with cooking spray, about 2 inches apart.  Press each ball flat with the bottom of a glass sprayed with cooking spray.
  7. Bake at 425°F for 5 to 6 minutes until the tops crack.  Cool on pan 3 minutes before transferring to wire rack to cool completely.

Filling Directions:

  1. Beat together confectioners’ sugar and shortening.  While beating add milk and vanilla extract and beat until fluffy.
  2. Spread some filling on the flat side of a cooled cookie and top with a second cookie.

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