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.

That’s how much I love you guys.

Of course, you don’t have to make the filling on peppermint whoppie 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!

I have a coworker (Hi Sam!) that is actually a master of the whoopie pie.  It’s a tricky balance with these guys so I decided to consult her as an expert.  She sent me a few recipes and I went to work.  I think they turned out pretty fantastic.

Pink Peppermint Whoopie Pies (Pie recipe from a Gourmet 2003 recipe.  Filling recipe from A Bon Appétit Dec. 2005 recipe.)
Makes about 18-20 pies depending on how big you make them.  You could half this recipe of course.

For cakes:
- 4 Cups all-purpose flour
- 1 Cup Dutch-process cocoa powder (high quality)
- 2.5 Teaspoons baking soda
- 2 Teaspoons salt
- 2 Cups well-shaken buttermilk
- 2 Teaspoons vanilla
- 2 sticks unsalted butter, room temp
- 2 Cups packed brown sugar
- 2 large eggs

For filling:
- 1.5 Cups (3 sticks) unsalted butter, room temp
- 3 Cups powdered sugar
- 1.5 Teaspoons peppermint extract
- a few drops of red food coloring

Making the 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 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 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, 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.

Bake these guys at 350 degrees 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.

Cool it down. 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.

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

Some whoopie filling recipes call for marshmallows, but I skipped that and just made a really thick butter cream 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.  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 confectioners 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 food coloring.  Just remember.  It’s easy to add more.  It’s impossible to remove it.

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.

I think you can probably imagine the next step, but it involves slathering on as much of this stuff as you want between two of your baked cookie-cake things.

Repeat.

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 – like this:

I brought these to a work lunch and they seemed to be popular.  I even got approval from the queen of whoopie pies, so you know they are good.