How to Make Chocolate Whoopie Pies Like a Pro

Even though multiple states are in disagreement over where they originated, whoopie pies are a mix between a cookie, pie, and cake from New England. Maine even made them the official state treat in 2011. But whether you side with Pennsylvania, Massachusetts, or Maine, one thing is undebatable: whoopie pies are delicious when they’re made right. 

Stacy Begin (who’s on Team Maine) is the owner of Two Fat Cats Bakery in Portland, Maine where whoopies are made fresh everyday. For a pie that’s only about three inches in size, I quickly learned from her that there is an art to making them. 

“Our whoopie pies look very traditional. They look like what we think here in Maine a whoopie pie should look like, but we're a little more involved and we use a different take,” she says. “We have the traditional chocolate cake and it's a really nice chocolatey flavor. But in the filling, we do not use shortening. What we use instead is a marshmallow buttercream so the texture is really silky smooth and I think that's what makes it a little different than what you might regularly find here in Maine.”

When making them from scratch, Begin says the cake itself has to be moist. “I even like it a little bit if it sticks to the roof of your mouth,” she adds. And a good filling is one that’s not too sweet but still full of flavor. After all, when you bite into one, you don’t want to be greeted with a mouth full of sugar. 

“The whoopie is just a really humble dessert or snack, so if it's a little messy, that's great. It shouldn't be too precious. It should be like you're dying to dig into it and you're licking your fingers and you've got crumbs around your mouth,” she says. “That's a good whoopie pie.”

While the whoopies at Two Fat Cats Bakery are made slightly differently, Begin created a recipe for two dozen classic ones that’s suitable for home bakers. Just in time for National Pi Day.

Makes about 24 whoopie pies 

Cake Ingredients

Filling Ingredients

Directions for cakes:

1. Preheat the oven to 350F. 

2. Melt the bittersweet chocolate slowly in a double boiler.  Let cool slightly.  While the chocolate cools, cream together softened butter and sugar until the mixture is light and fluffy. 

3. Then, slowly add the oil to the creamed mixture and mix well. Add the eggs one at a time and mix well scraping the bowl after each addition.  

4. Mix in the cooled chocolate until the mixture is combined and there are no chocolate streaks.  

5. In a separate bowl, combine all dry ingredients. Alternate adding dry mix and the buttermilk, starting and ending with the dry mix.  

6. Line 4 cookie sheets with parchment paper and scoop whoopie batter onto the parchment using a cookie scoop.  If you don’t have a cookie scoop, then scoop enough batter to equal 2-3 tablespoons per cake.  

7. Space out the scoops 3 across and 4 down to give you 12 whoopie cakes per cookie sheet.  

8. Bake at 350F for 10-12 minutes.  

9. Whoopies are done when you lightly press the top of the cake with your finger and it bounces back slightly.  Let cool completely before filling.

Directions for the filling:

1. Place the egg whites in the sparkling clean, grease-free bowl of your stand mixer. Add the cream of tartar and a pinch of salt and beat with a whisk attachment on high until the whites hold soft peaks. Slowly add ⅓ cup of the granulated sugar and beat until the whites are fairly stiff, but not dry. 

2. Place the remaining 1 cup sugar and ⅓ cup water in a small saucepan, and bring to a boil over medium high heat. Cook the syrup until the temperature registers 242°F on an instant thermometer. The syrup will be glossy and slightly viscous, with bubbles forming and popping at a steady, but not frantic, rate.

3. Immediately remove the sugar from the heat and pour about ¼ cups of it into the meringue. Turn the mixer on high and continue to pour the syrup into the meringue in a slow steady stream, taking care not to hit the whisk attachment. 

4. When all the syrup is incorporated, continue to beat the meringue on high until it is cool to the touch. 

5. With the mixer going, add the soft butter in large spoonfuls, beating until smooth after each addition. When all the butter is added, continue to beat until the buttercream is silky smooth. Beat in the vanilla extract. If at any time the buttercream gets soupy or separates, just keep beating. It will eventually come together.

6. To assemble the whoopie pies, flip one cake over and dollop 2-3 tablespoons of filling on to it (or more if you love a messy whoopie pie) and top with another cake.  Continue until all the cakes are assembled.  Then – enjoy!

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