Day #1 of Holiday Appetizers: Chocolate Peppermint Whoopie Pies

"Eat Dessert First." Good words to live by, if there ever were any. A cocktail party can't survive on savory stuff alone, and for good reason. The holidays are bursting at the seams with fabulous dessert flavors like gingerbread, egg nog, cocao and peppermint, just to name a few. For my cocktail party I opted for the latter, combining chocolate and peppermint in a miniature whoopie pie rolled in crushed candy cane pieces. I made 21 whoopie pies and they were gone before the party was halfway through, disappearing off the tray as quickly as I could bring them out!

Chocolate Peppermint Whoopie Pies

Here's how you make the Whoopie Pies. Don't forget to check back tomorrow for Day #2 of Holiday Appetizer Recipes: Mini Mac & Cheese Cups!

Chocolate Peppermint Whoopie Pies


  • 2 cups all-purpose flour
  • 1/2 cup unsweetened cocoa powder (see Note), sifted
  • 1 teaspoon baking soda
  • 1/2 teaspoon baking powder
  • 1/2 teaspoon salt
  • 1 stick unsalted butter, softened
  • 1 cup light brown sugar
  • 1 large egg
  • 1 teaspoon pure vanilla extract
  • 1 cup whole milk 


  • 2 sticks unsalted butter, softened
  • 2 cups confectioners' sugar
  • 1 vanilla bean, split and seeds scraped
  • One 7.5 ounce jar Marshmallow Fluff 
  • 3 drops peppermint extract
  • 1 cup crushed peppermint for rolling (gourmet versions available at Surfas, Sur La Table & specialty stores)

DIRECTIONS: Preheat the oven to 350° and line 2-3 large baking sheets with parchment paper. In a medium bowl, whisk the flour with the cocoa powder, baking soda, baking powder and salt. In the large bowl of a standing mixer with the whisk attachment (or use a handheld electric mixer), beat the butter and brown sugar at medium speed until fluffy, about 2 minutes. Add in the egg and vanilla and beat until combined. At low speed, beat in the dry ingredients and milk in three alternating additions; scrape down the side and bottom of the bowl as necessary.

Combine dry & wet ingredients 
Using a tablespoon, scoop 12 level mounds onto each baking sheet, about 1 1/2 inches apart. Bake the cakes in the lower and upper thirds of the oven for about 16 minutes, until risen and firm; shift the pans from top to bottom and front to back halfway through baking. Transfer the sheets to racks and let the cakes cool completely. In a large bowl, beat the butter with the confectioners' sugar, peppermint extract and vanilla seeds until fluffy. Beat in the Marshmallow Fluff. Scrape the filling into a pastry bag fitted with a large plain tip. Pipe the filling onto the flat sides of half of the cakes and close the whoopie pies, pressing to evenly distribute the filling to the edges.

Use a tablespoon to drop mounds of batter on each baking sheet

Bake for about 16 minutes

Beat filling ingredients in bowl of a standing mixer until fluffy
Using a piping bag and large star tip, pipe filling onto one half of each whoopie pie
Top with other half of whoopie pie and press gently until filling reaches edges

 Pour the peppermint pieces on a plate (or wide bowl) and gently roll the edges so the pieces stick to the filling. If the filling isn't all the way to edge of the cake, gently sprinkle the peppermint pieces on the filling with the your fingers. Refrigerate or freeze until ready to serve. Note: If your party is especially warm, consider freezing the pies so the filling doesn't melt and run out of the pies. The pies are equally delicious frozen, like a giant peppermint Oreo!

Gently roll in crushed peppermint pieces

Refrigerate or freeze on tray until ready to serve. Transfer to serving platter and enjoy!


  1. Yum! That filling could be great between those pre-made (gasp) chocolate wafers too I'm sure.

  2. Your version is slightly different than that I made last year...I like yours with the vanilla bean, and piping the filling looks so neat (mine were a bit of a mess, I must admit). Are you able to buy the peppermint pieces already crushed? I went through several baggies while attempting to crush candy canes with a rolling pin...it was comical.

  3. Tracy: Yes, for sure! That would be delicious.

    Penelope: I bought pre-crushed peppermint pieces that had already been sifted and were a consistent size. I also killed several baggies last year and ended up with peppermint dust amidst giant chunks. Buying pre-crushed this year was definitely worth it!


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