Peppermint Whoopie Pies

It’s not very often that I make something pink here at Macheesmo. It’s not a color that I’m very familiar with. But it’s the holidays and so I’m willing to step outside my comfort zone and make something tasty and pink like these Peppermint Whoopie Pies! 

That’s how much I love you guys.

Of course, you don’t have to make the filling on peppermint whoopie pies pink, but then they would just kind of look like a ginormous Oreo cookie. Not that that would be bad, but it’s just not what I was going for here.

Anyway, these turned out perfect!

What makes a good whoopie pie?

If you haven’t had a whoopie pie before, it is essentially two cookies with some sort of frosting smashed between them. The best ones, in my opinion, have a really soft cookie that is closer to a cake in some ways than a cookie. You don’t want a thin, crumbly cookie or the whole thing will just fall apart.

As far as the filling goes, a good buttercream frosting works well. I’ve also seen whoopie pies with marshmallow fluff and that can work well also. The key thing to remember about a whoopie pie is the ratio of cookie to frosting filling. If you end up using thinner cookies, use a thin layer of filling. Thicker cookies allow you add a thick layer of frosting!

Making the chocolate cakes

To me, what makes a delicious whoopie pie is a light, airy cake (and it actually is closer to a cake than a cookie or pie). It’s not always easy to get right though, but when you do, you will definitely exclaim, “WHOOPIE!”

To start, sift all your dry ingredients (flour, cocoa powder, baking soda, salt) into a large bowl. It’s important to sift here or whisk furiously to make sure your dry ingredients are nice and light.

Meanwhile, add your unsalted butter and sugar to a mixing bowl and cream them together. I let mine mix for about 3 or 4 minutes until it was very light. If you are using a hand mixer you might need to go even longer.

Next, mix in your vanilla and eggs. Then slowly add in your flour mixture and buttermilk in alternating stages to your creamed butter. As always with cake recipes like this, start with dry ingredients and end with dry ingredients. So it goes 1/3 of your flour, 1/2 of your buttermilk, 1/3 of your flour, 1/2 of your buttermilk, and finally the last 1/3 of your flour.

Then just mix it together on low until it all is combined. The last thing you want to do is over-mix this. If you do that you’ll have tough, chewy, very non-whoopie worthy pies.

Once it’s mixed well, spoon dollops of it onto a parchment paper-lined baking sheet. You could make these as big or small as you want, but just try to get them as uniform as possible.

I went for about 2 Tablespoon-sized cakes. Keep in mind they will grow quite a bit while baking so leave an inch at least between each pie. I got a bit sloppy with a few.

Bake these chocolate cakes in a pre-heated 350 degrees oven for 11-13 minutes. Rotate your pans once to make sure they cook evenly. They should be slightly springy when they are done.

Let them cool on the sheet for a minute or two and then move them to a wire rack to cool.

For some reason, it didn’t dawn on me that making 20 whoopie pies is actually baking 40 individual mini-cakes. I was able to do 8 per baking sheet so it took me 3 rounds of baking to finish them all using two baking sheets at a time. I went ahead and reused my parchment paper even though that’s apparently a no-no. I didn’t notice any difference in the later rounds of baking.

Cooling the cakes

It’s very important to make sure that your cakes are absolutely cool before icing them. Otherwise, your frosting will just melt and you’ll have sad little pink pools of butter.

I would let them cool to room temperature and then transfer them to the fridge until they are completely chilled and cool. 

Anyway, while they are cooling (or baking), you need to make this bad-ass pink peppermint frosting.

Making the Peppermint Buttercream Frosting

Some whoopie pie filling recipes call for marshmallows, but I skipped that and just made a really thick buttercream frosting. It worked great!

Start by adding your room temperature butter to your mixer and mixing it on medium until it is, well, creamy. Then add in your tiny amount of peppermint extract. Be careful with this stuff. It’s very potent and too much of it will turn your whoopie pie into an Altoid (not a good thing for a huge cookie).

Once your flavoring is added, slowly add in your sifted confectioner’s sugar. It’s a lot of sugar. Go slowly or you’ll end up with a layer of the stuff all over your kitchen.

That might happen anyway, but you can at least try to avoid it by going slowly.

Once you get all your sugar incorporated, add just drops of red food coloring. Just remember. It’s easy to add more. It’s impossible to remove it.

Finishing the Peppermint Whoopie Pies

Once your cakes and frosting are done, then it’s as easy as sandwiching the peppermint whoopie pies together! The amount of frosting you use for each is kind of up to you, but as a general rule I think about 1/4 inch of frosting is a good rule of thumb for each pie. 

If you wanted to you could add some crushed-up peppermint candies or crushed candy canes to the outside of the whoopie pies for some texture. 

You can of course go crazy with the frosting, but a little restraint is good I think. The frosting can be overpowering if you slather it on too thickly.

I like to go for a pretty even layer.

And after all that, you’ll end up with this lovely product, which might win the award for most colorful Macheesmo photo of the year.

These peppermint whoopie pies will be an absolute hit at any holiday party or on any holiday cookie platter!

Here are a few other recipes to try!

• Halloween Whoopie Pies
• Gingerbread Sandwich Cookies
• Homemade Peppermint Patties
• Gingerbread Crinkle Cookies from Grandbaby Cakes