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Whoopie Pies – Chocolate with Vanilla Cream

Another recipe from Pinehurst Inn Bed & Breakfast in Bayfield, Wisconsin.

We were in Portland, Maine a number of years ago and had one of the best whoopie pies ever, unfortunately I do not remember the name of the bakery. We just came upon it during one of our walks around town. I should have paid more attention but I was too focused on what I was eating. Since then, I have been obsessed with whoopie pies and have tried many many recipes until I found one that had just the right springiness in the “cake” and then, with a few tweaks, I was able to find the perfect balance of flavors (at least from my perspective). Here is our current favorite chocolate vanilla cream whoopie pie recipe, which is essentially the whoopie pie recipe from Cooking Classy with a couple of changes. I use a vanilla buttercream filling instead of the marshmallow cream filling from Cooking Classy as I find the marshmallow cream a bit too sweet for my liking. I sometimes fill them with a vanilla whipped cream cream cheese filling which also is incredibly indulgent, but I am reserving that filling for a spiced whoopie pie that I am still working on. 

We like to provide our guests an afternoon treat at Pinehurst Inn Bed & Breakfast, which varies from day to day–just a little surprise after a day of exploring and playing in and around the Bayfield, Wisconsin area. These chocolate whoopie pies likely will make the afternoon treat rotation this summer. We hope our guests enjoy these whoopie pies as much as we do. Thanks for checking in with us.

Becky and Mike

Prep Time: 45 Minutes
Cook Time: 10 Minutes
Total Time: 55 Minutes
Servings: 16-18


  • 2 cups all purpose flour
  • 1/2 cup unsweetened cocoa powder
  • 1 tsp baking soda
  • 1/2 tsp salt
  • 1 cup brown sugar
  • 1/2 cup buttermilk
  • 1/2 cup vegetable oil
  • 1 TBLSP vanilla extract
  • 1 large egg
  • 1/2 cup hot coffee
  • 1/2 cup butter (1 stick), room temperature
  • 2 1/4 cups powdered sugar
  • 2 TBLSP whipping cream
  • 1 tsp vanilla extact
  • pinch of salt


  1. Preheat oven to 375 degrees. Line 3 baking sheets with parchment paper (or silicone mats).

  2. In a medium bowl, whisk together flour, cocoa powder, baking soda, and salt and set aside.

  3. In stand mixture bowl (or large bowl with a hand mixer), mix together brown sugar, buttermilk, vegetable oil, vanilla, and egg until smooth. Add flour mixture and mix until just combined. Add hot coffee and mix to fully incorporate but be careful not to overmix.

  4. Using a 1.5 tablespoon scoop, scoop batter onto prepared baking sheets about 2 inches apart. Bake 8-10 minutes until the top springs back when touched or when toothpick comes out clean. Let pan cool on baking rack.

  5. For filling, place butter in medium bowl and with a hand or stand mixer mix until smooth (about 1 minute). Add powdered sugar, whipping cream, vanilla, and salt and mix on low for about 1 minute, then mix on high for about 3 minutes (it will be light and fluffy).

  6. Assembly: place filling into piping bag with large round tip (a large baggie with corner snipped will work as well). Turn half the cakes/cookies upside down and pipe filling to cover bottom. Top with remaining cakes/cookies. Serve immediately or wrap in plastic wrap and store in refrigerator until ready to eat. Enjoy!

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