These Old Fashioned Whoopie Pies are straight from my momma’s recipe box. The wafer cookies are rich and chocolatey, while the creamy vanilla filling is light, sweet, and smooth — resulting in the perfect sandwich cookie perfect for special occasions like holidays, birthdays, graduations, or even just plain ol’ weekends!

Take this recipe up a notch by using my Homemade Vanilla Extract recipe!

Momma’s Old Fashioned Whoopie Pies

Who remembers Whoopie Pies? These are my Momma’s Old Fashioned Whoopie Pies, and I could never resist these soft chocolate sandwich cookies filled with a layer of fluffy white frosting.

My mom would make these on special occasions for my sister and I, like our birthdays, sports events, family celebrations, or just because I would beg her to make them long enough until she finally caved. (Sorry, not sorry, Mom!) Regardless of the catalyst behind the making and baking of these beauties, my eyes would always get as big as the whoopie pie when I saw them.

I came across her recipe while going through my treasured recipe box, and all the memories flooded back. The smell, the way they tasted, her raised eyebrow when I would inevitably try to sneak one. It’s so incredible how food is intertwined with memories.

I made a new memory when I made these to celebrate her birthday this year. I piled them up and topped the whole thing off with a candle a la a very nontraditional birthday cake. I cried the whole time — not gonna lie — but I’m glad I made them. And they were just as delicious as I remembered!

What Is a Whoopie Pie?

Is it a cake, a cookie, or a pie? That is the question …

Momma’s Old Fashioned Whoopie Pies are soft sandwich cookies filled with a creamy filling. They’re more like a cake-cookie, if you ask me, but I will not argue with what to call them as long as I get to eat them!

The original and most commonly made whoopie pies are chocolate, but because we humans can’t leave well enough alone you can find many seasonal variations on the original like red velvet or pumpkin whoopie pies, probably served alongside a giant pumpkin spice latte (which I wouldn’t hate!).

Traditional whoopie pies are made with vegetable shortening, not butter. These are most definitely old school and shortening rules supreme here. You can search up a substitute if that isn’t your thing, but I beg you to try it this way at least once. This recipe may just change your mind!

You may have also heard them referred to as black moons, gobs, blacks-and-whites, bobs, or BFOs (that’s short for Big Fat Oreo). But for me, they will forever be Momma’s Old Fashioned Whoopie Pies.

Who Invented Whoopie Pies?

Originally popular in New England and around Amish country, whoopie pies are a throwback treat that are hard to resist. For even more fun, you could tint the filling (say red for Valentine’s Day, Green for St. Patty’s Day, etc.) and roll it with sprinkles.

Who doesn’t love sprinkles. Amiright?

How To Store Whoopie Pies

If you’re not assembling your whoopie pies immediately (this is foreign to me), follow these instructions for storing them and enjoying at your leisure:

To Store: Once baked and completely cooled, cover the chocolate cookies with plastic wrap, and they should keep at room temperature for up to three days. Once filled, store them in an airtight container in the refrigerator. But to be completely honest, mine have never lasted more than a day or two because they’ve been devoured, so I don’t have much experience in this department!
To Freeze: Bake chocolate cookies and prepare the filling, then freeze separately. Allow to thaw overnight in the fridge and come to room temperature before assembling.

How To Make Homemade Whoopie Pies

Preheat oven to 350 degrees, and prep a rimmed baking sheet by lining with a silicon mat or parchment paper.
Combine shortening, sugar, and eggs until creamy in the bowl of your stand mixer.
Sift dry ingredients — flour, cocoa powder, baking powder, baking soda, and salt — in a separate bowl while sugar mixture is creaming.
Add dry ingredients to stand mixer alternating between flour mixture and milk. Add vanilla, and mix by hand to combine.
Scoop cookie dough onto baking sheet using a small cookie scoop — eight per sheet.
Bake for approximately 10 minutes. Allow to cool completely.
Spread desired amount of whoopie pie filling onto half of the cookies.
Top with additional cookie to create sandwich (aka your whoopie pie). Enjoy!

Key Ingredients for Whoopie Pies

Shortening: Staying true to the traditional way to make whoopie pies, this recipe calls for vegetable shortening instead of butter.
Granulated Sugar: Plain ol’ white granulated sugar is the perfect sweetening agent for these chocolate cookies!
Eggs: Two do the trick for these whoopie pies. Just make sure to lightly beat before adding to dough mixture.
Dry Ingredients: Sift all-purpose flour, cocoa powder, baking powder, baking soda, and kosher salt in bowl to add to wet ingredients.
Whole Milk: This is one aspect of the recipe that gives the cookies a cake-like texture.
Vanilla Extract: Go with pure vanilla extract over the imitation stuff. Or better yet, make it yourself! Learn how below.

TIP: Make your own vanilla extract … It’s easier than you think and well worth the effort. You’ll use it more than you imagine! It also makes a great gift, especially during the holidays.

More Dessert Recipes To Try

If you liked my Momma’s Old Fashioned Whoopie Pies, then you’ll love these other dessert recipes:

It makes our day when you recreate any of our recipes. If you do, please consider leaving a star rating on this recipe, take a photo and TAG me on Instagram with #bellalimento. We would love to see them!

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Momma's Old Fashioned Whoopie Pies

These Old Fashioned Whoopie pies are a classic dessert from two soft chocolate sandwich cookies filled with a layer of fluffy white frosting.

Ingredients

1/2 cup shortening
1 cup granulated sugar
2 eggs - beaten
2 cups all purpose flour
5 tablespoons cocoa powde
r1 teaspoon baking powder
1 teaspoon kosher salt
1 cup whole milk
1 teaspoon baking soda
1 teaspoon pure vanilla extract

Instructions

Preheat oven to 350 degrees. Line a rimmed baking sheet with a silicon mat or parchment paper.
Into the bowl of your stand mixer cream together shortening, sugar and eggs.
Sift flour, cocoa powder, baking powder, baking soda and salt.
Add to stand mixer alternating between flour mixture and milk. Add vanilla. Mix to combine.
Using a small cookie scoop. Scoop onto baking sheet 8 per sheet. Bake for approximately 10 minutes. Allow to cool completely.
Place desired amount of whoopie pie filling onto half of the cookies.
Top with additional cookie to create sandwich (whoopie pie).