Best Ever Chocolate Whoopie Pies
I decided it was time to introduce my almost 3-year-old granddaughter to a classic dessert—the almost universally beloved whoopie pie. If you, too, for some strange reason have never had a whoopie pie, then you’re in for a very delicious treat!
Whoopie pies (which are called “gobs” in some parts of the country) are not actually pies. They are what I would call cakey cookies which are used to sandwich a fluffy, marshmallow-y filling. Some whoopie pie recipes call for a simple buttercream frosting as the filling, and others use an Italian meringue buttercream for the filling. For me, it’s a Marshmallow Fluff filling all the way.
When my hubby Roger saw what I was making, he told me he didn’t really like whoopie pies. In my opinion, that borders on being sacrilegious. After they were made, I gave him a bite of mine. Boy, did his opinion do an about face! After he scarfed down a whoopie of his own, he was ready to go after a second one. Let’s just say he’s found religion, lol.
Through the years, I have made chocolate whoopie pies from a 50-year-old recipe given to me by a friend. While those whoopie pies were very good, I recently found a recipe for the cookie part that is even better. I paired it with my favorite whoopie pie filling from my s’mores whoopie pies, and the results were simply frantastic! The “pies” are dark chocolate, moist and fudgy. Combined with the light and fluffy filling, it is the best whoopie pie I have ever had in my life.
I told my granddaughter that whoopie pies got their name because whenever kids saw that their moms or grandmothers* had made some, they would jump up and down and say, “Whoopie!” Now, I don’t know if that’s true or not, but that’s my story and I’m sticking to it.
*Not to slight fathers and grandfathers!
Just a word of advice…be prepared to wash sticky little fingers and mouths because these whoopie pies are deliciously gooey. 
Best Ever Chocolate Whoopie Pies
Makes 15 to 16 whoopie pies
Ingredients for Whoopie Pies
- 2 cups flour
- 1/2 cup unsweetened cocoa powder, sifted
- 1 1/4 tsp. baking soda
- 1/2 tsp. salt
- 1/2 cup (1 stick) unsalted butter, softened
- 1 cup sugar
- 1 egg
- 1 tsp. vanilla
- 1 cup milk
Ingredients for Marshmallow Filling
- 1 cup (2 sticks) unsalted butter, at room temperature
- 2 cups confectioners’ sugar
- One 7-oz. jar Marshmallow Fluff
- 2 tsp. vanilla extract
Directions for Whoopie Pies
Preheat oven to 350o F and line two (or three) baking sheets with parchment paper.
In a medium bowl, whisk together the flour, cocoa powder, baking soda and salt. Set aside.
In the bowl of an electric mixer fitted with the paddle attachment, cream butter and sugar until light and fluffy. Add egg and vanilla. Beat until well combined. Gradually add in the milk, scraping the bottom of the bowl as needed. The batter might curdle but don’t worry. It will come together when you add the dry ingredients.
Slowly add dry ingredients. Mix until just combined.
Using a 1-oz. (2-tbl.) cookie scoop, drop the batter onto the prepared baking pan 2″ apart. Bake for 6 to 8 minutes or until a toothpick inserted into the center comes out clean. Let cool completely before frosting.
Directions for Filling
In the bowl of a stand mixer fitted with the paddle attachment, beat the butter on medium-high speed until smooth, about 1 to 2 minutes. Add the confectioners’ sugar and beat until incorporated. The mixture will become crumbly at first; just keep beating and it will come together. Add the Marshmallow Fluff and vanilla and beat until light and fluffy, about 2 to 3 minutes.
When the whoopie pies have cooled completely, spread or pipe the filling onto the flat side of half the cookies. Sandwich with remaining cookies, pressing down slightly so that the filling spreads to the edge of the cookies.
Notes
I used a 2-tbl. cookie scoop, and my whoopie pies were approximately 2 1/2” in diameter. If you use a smaller cookie scoop, you will most likely have to adjust the baking time. Personally, I wouldn’t use less than a 1 1/2” cookie scoop.
Leftovers can be stored in an airtight container lined with wax paper at room temperature for 2 to 3 days and in the fridge for up to 5 days. Bring to room temperature before serving.
To Freeze – Individually wrap the whoopie pies and store them in the freezer for up to 3 months. Thaw overnight on the counter before serving.
Source: Cookie part from Little Sweet Baker. Filling from Fran’s Favs