Chocolate Whoopie Pies

Yup, it’s a chocolate whoopie pie post; and I know what you’re thinking: they’re totally kind of last year. But I love them — which makes sense in light of the fact that I am a chocolate cake with vanilla frosting fanatic, and back in the day I was all about a Hostess Suzy Q or a Drakes Devil Dog, two very whoopie-ish packaged treats from my late 70s/80s childhood. Moreover, even when my whoopie love has been tested, I’ve remained steadfast. (While working at Baked, I always opted to celebrate my bday with a chocolate whoopie pie (or several), even when offered any cake of my choosing).

Chocolate Whoopie Pies | Jessie Sheehan BakesFunnily enough, despite my deep affection for chocolate whoopie pies, I hadn’t really thought about developing my own recipe for them until this past summer. I was visiting with one of my husband’s brothers when he described making the most amazing whoopie pies with my mother-in-law (aka Nonnie), when he was little. I recalled that I had Nonnie’s recipe for said whoopies stashed in my folder at home, and using it as my jumping off point, went to work on some whoopie pie-reconnaissance soon after. Not surprisingly, my initial recon unearthed my mother-in-law’s whoopie pie recipe in Bon Appetit. since my intention was to tweak and fiddle anyway, I was nonplussed by the discovery, and tweaking began in earnest.

Chocolate Whoopie Pies | Jessie Sheehan Bakes

I wanted my own recipe to include yolks, instead of whole eggs (like Nonnie’s) for moisture, and also shortening to keep the pies from spreading while baking (like Nonnie’s again, and like Martha Stewart’s whoopie pies and from the book, Whoopie Pies written by the editor at Chronicle Books of the soon-to-be released cookbook, Icebox Cakes, co-authored by yours truly), I decided upon dark brown sugar as my sweetener, for moistness again and for that caramel-y/molasses-y flavor-thing. I chose buttermilk (influenced again by Matt and Nato), rather than milk, as my liquid, because I love its tang. the recipe for chocolate whoopie pies in the book, American Desserts, inspired me to amp up the amount of cocoa powder in my recipe, but once I did so, I added a bit of extra fat (in the form of butter) to compensate for cocoa’s drying nature. Additionally, I decided to bloom the cocoa powder in boiling water and add a bit of espresso powder in order to truly make the chocolate-y nature of these pies sing.

Chocolate Whoopie Pies | Jessie Sheehan Bakes

And sing they do. They are perfect little uber-chocolate-y cakes, filled with my traditional old-school buttercream frosting (however, feel free to prepare them with whatever filling you would like — at Baked they fill them with Swiss meringue buttercream). Yes, I realize that I could have spiced things up a bit (figuratively and literally) with a flavored filling (chocolate cardamom whoopie pies anyone?), but for me, these whoopies are all about having once been a girl who loved Suzy Qs, and I’ve never seen said snack-cakes filled with anything but a delightfully, fluffy, vanilla-flavored cream.

Buttercream frosting recipe.

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Chocolate Whoopie Pies

Recipe Author Jessie Sheehan
Course Dessert


  • 1 3/4 cup all purpose flour
  • 1 tsp baking powder
  • 1/2 tsp baking soda
  • 1/4 tsp salt rounded
  • 1/2 cup shortening
  • 2 Tbsp unsalted butter room temperature
  • 1 1/4 cup packed dark brown sugar
  • 2 egg yolks
  • 1 Tbsp pure vanilla extract
  • 3/4 cup dutch processed cocoa powder
  • 1 tsp espresso powder
  • 1/2 cup boiling water
  • 3/4 cup buttermilk room temperature


  • Preheat the oven to 350 degrees.
  • In a medium-sized bowl, whisk the flour, baking powder, baking soda and salt together and set aside.
  • In the bowl of a stand mixer, fitted with the paddle attachment, combine the shortening, butter, and sugar, and mix on medium-low speed until slightly fluffy, scraping down the bowl with a rubber spatula, as needed. Add the yolks and vanilla and mix again on medium low until just incorporated.
  • Place the cocoa and espresso powders in a small bowl and add the boiling water. Whisk until combined and add this chocolate mixture to the stand mixer bowl and mix on medium low to combine, scraping down the bowl with a rubber spatula as needed.
  • Add the dry mixture in three additions to the stand mixer bowl, alternating with the buttermilk in two additions, and ending with the dry. Take the bowl off the mixer when there is still unincorporated flour in the dough and finish mixing by hand with a rubber spatula. Let the dough rest on the counter, lightly covered with saran wrap, for at least 30 minutes.
  • Line two baking sheets with parchment paper and drop tablespoons of dough about 1-inch apart on the sheets. Bake for 8 to 10 minutes, rotating the pans halfway through the baking time until the cookies are dry to the touch and bounce back when lightly pressed. let cool completely before filling with tablespoons of the above buttercream frosting, or one of your own choosing.
  • Serve immediately, or cover with saran wrap and refrigerate for up to 24 hours. Bring to room temp before serving. Whoopie pies are best consumed within 2 to 3 days.

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