When I was a little girl, my grandmother made these amazing Whoopie Pies every summer when we visited and it remains a favorite memory of mine. If you’ve never had a whoopie pie, you’ve simply been missing out. 🙂 Whoopie Pies have a rich chocolate cake-like cookie on the outside and a uniquely creamy, not overly sweet cream filling on the inside. Some whoopie pies are made with marshmallow fluff as the filling. As much as I LOVE marshmallows and marshmallow fluff, it doesn’t seem like a real whoopie pie with the fluffy cream filling.
Making whoopie pies can be somewhat of a time consuming project. I don’t make these very often because of the time it takes, but I think that makes them extra special. This recipe makes a lot, which is nice if you are making them for a crowd.
I like to start a little bit out of order and work on part of the filling first because one of the key components of the filling is a flour and milk cooked mixture. I know it sounds strange and a little like the glue you may have used in elementary school, so you’ll have to trust me on the this one – it’s key to making the filling creamy and not overly sweet. This mixture needs to be cooked and then cooled, so if we make this part first, it can cool while we’re making the cookies.
In a small saucepan, whisk together 1 cup of milk with 5 Tbsp. of flour.
Cook this over medium heat, whisking constantly until it gets nice and thick and starts to bubble. Cook for another minute or so, whisking the whole time, then take off the heat and let cool.
Whisk it every now and then while it cools to room temperature so that the top doesn’t get dried out. Once it is room temperature, cover it with wax paper, placing the wax paper right on top of the mixture to ensure the top does not dry out. Place this in the refrigerator while making the cookies.
We’ll finish the rest of the filling when we are ready to put the whoopie pies together. Next, let’s start on the cookies.
Add the butter and sugar to the bowl of the mixer and beat on medium speed until light and fluffy.
Add the eggs and vanilla. Mix well on medium-low speed.
Add the flour, cocoa, and baking soda. Mix on low speed until completely mixed.
In a measuring cup, add 1 tsp. of vinegar to 1 cup of milk. Add this and 1 cup of hot water to the batter. Mix well. Once mixed, beat on medium-high speed until smooth.
Pre-heat the oven to 425 degrees. Drop spoonfuls of batter onto greased cookie sheets. I use about a tablespoon of batter for each cookie because it seems to be a nice manageable size.
Bake in the oven for 8-10 minutes. If using airbake cookie sheets, bake for about 12 minutes.
Cool on a wire rack(s) and repeat the process until all the batter is used up. I think the last time I made these it made about 8 cookie sheets full. You need 2 cookies per whoopie pie, so it does take a lot of cookies to make a lot of whoopie pies. This part gets a little tedious for me – there are whoopie pies all over the kitchen on multiple cooling racks and plates by the time I am done making these. 🙂
Once the cookie process is done, it’s time to put the filling together. In the bowl of the mixer, add 1 cup of butter, 1 cup of sugar, and 2 tsp. vanilla extract. Mix this well on medium-high speed.
Add in 2 cups of confectioners sugar and mix again until light colored and fluffy. This can take a while, so be patient – lighter and fluffier is better than under mixed.
Slowly add the cooled milk and flour mixture, one spoonful at a time, stopping to scrape down the sides of the bowl between every couple of spoonfuls. Mix it on a medium to high speed until all the milk/flour mixture is completely incorporated. Mix it on medium high until nice and fluffy and light.
Now we are ready to put the whoopie pies together. Spread some filling on one cookie and top it with another cookie.
Just keep spreading the filling and topping with another cookie until they are all matched up. Serve and enjoy. If there are left-overs, keep them in the refrigerator. These never last long in our house. 🙂
- 2 cups sugar
- ¾ cup butter (1½ sticks)
- 1 cup unsweetened cocoa
- 2 eggs
- 2 tsp vanilla extract
- 4 cups flour
- 2½ tsp baking soda
- 1 cups milk plus 1 tsp. vinegar
- 1 cup hot water
- 1 cup milk
- 5 Tbsp flour
- 1 cup butter (2 sticks)
- 1 cup granulated sugar
- 2 cups confectioners sugar
- 2 tsp vanilla extract
- In a small saucepan, whisk 1 cup milk with 5 Tbsp flour.
- Cook over medium heat until thick and bubbly, then cook for another minute.
- Remove from heat and let cool.
- Once cooled to room temperature, cover with wax paper and refrigerate until ready to use.
- Pre-heat the oven to 425 degrees.
- Mix the sugar and butter until light and fluffy.
- Add the eggs and vanilla extract and mix until well combined.
- Add the dry ingredients, mix well.
- Add the milk and hot water, mix well.
- Beat on a medium-high speed until smooth.
- Drop spoonfuls of batter onto a greased cookie sheet.
- Bake at 425 degrees for 8-10 minutes.
- Cool on wire rack.
- Beat the butter and sugar until fluffy.
- Add the confectioners sugar and vanilla extract and beat until light and fluffy.
- Gradually mix in the cooled flour/butter mixture, one spoonful at a time until completely mixed, making sure to scrape down the sides of the bowl on occasion.
- Once mixed, beat on a medium-high speed until light and fluffy.
- Spread the filling on one cookie and top with another.
- Continue until the cookies are all filled.
- Serve. Refrigerate left-overs.