Making Whoopie (Pies)!

It was recently Joe’s 30th bday! Last year, I made Joe a chocolate cake. Normally a sure-fire win. But in a new apartment and a new oven? Let’s just say it looked pretty, but had “crispy” edges…that’s what happens when your oven is consistently 50F over the temperature you set it to!

What a goober. 🙂

So instead of the standard cake or cupcake, I decide to make something a little more out of the ordinary… a duo of Whoopie Pies!  Banana & Cream and Peanut Butter & Chocolate.

After the experience, I can heartily recommend not making both of these recipes at once. It makes a giant mess and dirties up almost every mixing bowl you own. (I believe it was 7/9 of my bowls.) Plus they made a TON of cookies at the scoop size I used. Luckily, the folks at lab and at Joe’s bday celebration were a fan so I didn’t have to eat them all!

I’ll start with the Peanut Butter Whoopie Pie!

Directions: Preheat the oven to 375°F and line your baking sheets with parchment paper. In a medium bowl, mix the dry ingredients (flour, baking soda and powder, and salt). In a large bowl, cream the butter, brown sugar, and peanut butter with a stand or hand mixer until smooth. (If your peanut butter is super stiff, you can try microwaving it for 5-10 seconds to loosen it up before you try to cream it.) Beat in the vanilla extract. Then add the eggs, one at a time.

Add in about 1/3 of the dry ingredients and mix in until just incorporated. Add half of the buttermilk and mix until combined. Scrape the sides of the bowl to make sure there aren’t pockets of flour or buttermilk hidden in there.

Repeat with the next 1/3 of the dry ingredients and the remaining buttermilk. Scrape the sides again. Finally, add the last 1/3 of the dry ingredients. Dough done!

Now here is where you have options for cookie size! I used a tablespoon and a 1/2 tablespoon to make large and small cookies. Keep in mind that you will eventually sandwich 2 cookies together, so you don’t want to make them TOO big. I made a mix of the two sizes because I know several folks on diets and I wanted everyone to be able to enjoy the pies!

No matter the size you choose, use your spoon to scoop the dough and a second soup spoon to help form the dough into a ball. Place the cookies about 1″ apart on the parchment-lined cookie sheet. Bake for 12-14 minutes (this baking time doesn’t really change by size, for whatever reason). But since everyone’s oven is different, to check that they are done, poke a toothpick through the center of a cookie. If the toothpick comes out clean, they are done.

Remove the cookies from the cookie sheet and cool them on a wire rack. Continue the scoop-n-bake process until you’ve made it through all of your dough. Let the cookies cool ALL THE WAY on a wire rack. If you try to add the filling while too hot, it will just melt and make a big mess.

And here are my different sizes.

Now for the filling..

Directions:  In a small bowl, measure out the cocoa, chocolate chips and salt. Bring the heavy cream to a simmer. I chose to do this in the microwave in a microwave-safe glass bowl. You just want the cream to barely reach a boil. If you’ve ever scalded milk, you’ll know why. (Yuck.) So just look for little bubbles and cream that is hot to the touch. Pour the hot cream over the cocoa-mixture and stir until smooth. Add the vanilla extract, and set aside to cool to room temp.

In a large bowl, cream the butter and crisco with 2 C of the powdered sugar. It will look terrible at first and like it will never come together. Just wait. It will happen in an instant! Just keep going until it is smooth.

Add half of the cooled chocolate mixture and beat until well mixed. This won’t happen unless you also have a spatula nearby to scrape the sides. It will be pretty obvious when it is well mixed.

Add the remaining chocolate and remaining 2 C of powdered sugar and beat until fluffy. At this point it will be fluffy but perhaps a bit stiff. So to help make it a bit more spreadable, add some milk, a tablespoon at a time, until you have a nice consistency.

Assembly: Now to make the whoopie! Make sure your cookies are at room temperature. Transfer the filling into a freezer bag and cut off the tip to make a piping bag. Then pipe about 1-2 T of the filling onto one cookie. Find a similar sized cookie, and make your sandwich! Easy as whoopie pie.

Now for the Banana Whoopie Pies!

Directions: For this recipe, you’ll want to turn down your oven to 350°F and re-line your cookie sheets with fresh parchment. In a 2 C measuring cup, mash your ripe bananas with a fork. You can use freshly ripe bananas or rippened bananas that you stowed in the freezer. Yes, freezing ripe bananas is an excellent way to store then for the next time you want to bake with bananas. I strongly suggest peeling them before freezing, because it can be a real mess trying to get the peel off a frozen, extra-gushy banana.

In a medium bowl, mix the dry ingredients (flour, soda, and salt). In a large bowl, cream together the butter and sugars until light and fluffy. Add the vanilla extract and mashed bananas. At this point, the mixture will look truly strange…curdled almost. That’s fine. Just keep going!

Add the dry ingredient mix to the banana mixture, and mix until well incorporated. Make sure there aren’t any hidden pockets of flour by scraping the edges and bottom of the bowl. Stir in the chocolate chips and your dough is done!

Scoop the dough as described above onto the cookie sheets and bake for 12-14 minutes. Again, you’ll know if the cookie is done when you can pull out a clean toothpick. Transfer the cookies to a wire rack to cool completely.

Now for the filling…

Directions: Beat the cream cheese, vanilla, and powdered sugar together until smooth and slightly whipped. Add enough milk to make the mixture spreadable.

Assembly: Just as before, lets make some whoopie! Make sure your cookies are at room temperature. Transfer the filling into a freezer bag and cut off the tip to make a piping bag. Then pipe about 1-2 T of the filling onto one cookie. Find a similar sized cookie, and make your sandwich! Easy as whoopie pie.

So my favorite?

Banana cookie > Peanut Butter cookie: Although both cookies are good, the banana cookie just turned out so moist! I couldn’t help going back for 2nds… But both were definitely good!

Chocolate filling >>> Cream cheese filling: The fillings, in my opinion, had a clear winner. This chocolate filling was really awesome for several reasons. (1) Much easier to work with. It wasn’t sticky, which made piping it mega easy. (2) Rich rich rich flavor without being too sweet. (3) Light consistency.  Unfortunately, the cream cheese filling WAS sticky and potentially too sweet (again, for my taste). Other folks didn’t seem to mind, but I think I was biased after making that chocolate filling 1st.

General crowd favorite was mixed! But I think the bday boy liked the peanut butter whoopie pie best 🙂

And next time I make these, i think I will leave out the chocolate chips from the banana whoopie cookie and use the chocolate filling instead.

Enjoy!

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