Cakespy: Whoopie Pie Cupcakes Recipe


Quirky, cute, sometimes controversial, always delicious recipes from Jessie Oleson.

Cakespy: Whoopie Pie Cupcakes Recipe

Jessie Oleson (aka Cakespy) drops by every Monday to share a delicious dessert recipe. —The Mgmt.

[Original artwork and photographs: Jessie Oleson]

Whoopie pies are not the next cupcake...or are they?

At the recent CupcakeCamp Seattle event, one cupcake submission (by talented amateur baker Audrey M.) made my eyes go wider than any other: the whoopie pie cupcake. Here it was: cold, hard proof that both are improved when combined. Yes!

Needless to say it was love at first bite, and I rushed home to try and recreate the magic in my own kitchen. I whipped up a batch of whoopie pie batter (using butter instead of the traditional shortening) and baked about two-thirds of it in cupcake cups, and the rest as regular whoopie pie cookies, and then sandwiched it all together with a generous dab of fluffy frosting.

The conclusion? Whoopie pies and cupcakes are definitely better together.

This recipe is adapted from the version found in the great cookbook All American Desserts, in which the recipe intro notes that "I got this recipe from a neighbor in Burlington, Vermont, the year before we moved out and Ben and Jerry (of ice cream fame) moved in".


Whoopie Pie Cupcakes

  • Yield:about 12 cupcakes


  • For the cupcakes and cookie tops:
  • 2 1/4 cups flour
  • 1 1/4 cups granulated sugar
  • 1/2 cup unsweetened cocoa powder
  • 1 teaspoon baking soda
  • 2 teaspoons cream of tartar
  • 1 teaspoon salt
  • 2/3 cup butter
  • 2 large eggs
  • 2 teaspoons vanilla extract
  • 1 cup milk
  • For the filling:
  • 1/2 cup unsalted butter at room temperature
  • 1 1/2 cups marshmallow fluff
  • 1 teaspoon vanilla extract


  1. 1.

    Preheat oven to 350°F. Prepare two baking sheets: one muffin tin and one cookie tray. Line the muffin tin with cupcake liners, and the cookie tray with a sheet of parchment.

  2. 2.

    Sift together the flour, sugar, cocoa, baking soda, cream of tartar, and salt into a medium-sized mixing bowl. Set aside.

  3. 3.

    With an electric mixer, cream the butter, eggs, and vanilla together in a large mixing bowl until light and lemon-hued. Add the dry ingredients bit by bit, alternating with the milk until your batter is smooth.

  4. 4.

    Using either a cookie scoop or by heaping teaspoons, drop 12 rounds of cookie dough on the cookie sheet, leaving about an inch and a half around each mound of dough. Try to size them so that they are slightly smaller than the circumference of the cupcake cups you are using.

  5. 5.

    With the remaining cookie dough, fill the cupcake cups. This should be enough batter to fill each cupcake cup about 2/3 full.

  6. 6.

    Bake until lightly browned around the edges (these are a lighter cocoa color than some whoopie pies so you will see light browning). For the cookie tops, this will be 8-10 minutes; for the cupcakes, this will be about 15-20 minutes (a toothpick inserted in the cake should come out clean). I baked both at the same time, simply taking out the tops sooner and leaving the cupcakes to bake a bit longer.

  7. 7.

    Let the cupcakes and cookie tops cool completely.