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Why These Chocolate Peppermint Whoopie Pies are the Perfect Valentine’s Day Treat

It's Sweet to Share!

chocolate peppermint whoopie pies

Originally Posted 2009 | Updated 2021

Valentine’s Day is all about the whoopie… but there are lots of ways to make love, and these cookies are just one of the best. 

What is there left to say except pull back the sheets baby…

Chocolate Peppermint Whoopie Pies

Whoopie Pies taste much more like cake then they do like cookies, however they look more like cookies than they do like cake. 

chocolate with peppermint whoopie pie

Why Are These Called Whoopie Pies?

It’s the exclamation you make when you bite into them! “Whoopie, these are sooo good!” 

That’s exactly what makes this the perfect recipe for Valentine’s Day!

chocolate peppermint whoopie pies

Chocolate Peppermint Whoopie Pies

Catherine Olson
Old Fashioned Chocolate Whoopie Pies filled with Pink Peppermint Frosting
Prep Time 45 mins
Cook Time 15 mins
Course Dessert
Cuisine American
Servings 12 Pies


Whoopie Pie Cookies

  • 1 cup butter
  • 2 cups brown sugar
  • 2 teaspoons vanilla
  • 2 eggs
  • 4 cups flour
  • 1 cup cocoa powder
  • 2 ½ teaspoons baking soda
  • 2 teaspoons salt
  • 2 cups buttermilk


  • 2 cups powdered sugar
  • 1 stick butter
  • 6 oz. sweetened condensed milk
  • 1 teaspoon vanilla
  • Red Food Dye
  • ¼ cup cocoa powder for chocolate frosting


Whoopie Pie Cookies

  • Cream together butter and sugars several minutes until light and fluffy
  • Add vanilla and eggs
  • Mix until just incorporated
  • Sift dry ingredients and add to butter and sugar alternately with buttermilk in 4 segments, mixing just until combined with each addition
  • Let dough rest for 10 minutes
  • Spoon even sized dollops onto baking sheet
  • Leave space between each dollop and use fingers to round out each cookie round
  • Bake at Fahrenheit 350°, 13-15 minutes until cookies have a defined dome
  • Transfer to wire rack to cool


  • Beat all ingredients together with hand mixer until smooth and creamy
  • Add food coloring until desired color is reached


  • When cooled, add a large spoonful of frosting to the bottom of one cookie
  • Cover with another cookie and gently squeeze until cookies are firmly attached
  • Optional: Dip chocolate filled whoopie pies halfway in melted Peppermint Hershey’s Kisses
  • Optional: Dunk outside of cookie frosting in crushed peppermint


Recipe originally inspired by Macheesmo
Keyword Chocolate Peppermint Whoopie Pies
whoopie pie dipped in peppermint chocolate

What Other Types of Frosting Can You Use?

You can fill your cookies with any type or flavor of frosting, but you want to make sure that it is thick enough to hold it’s shape. 

The possibilities are endless! 

Think of whoopie pies the same as you would macarons. Whatever you could think to fill these with, you can! 

Other Whoopie Pie Flavors 

  • Chocolate with Blueberry Frosting Whoopie Pies 
  • Chocolate & Tart Lemon Whoopie Pies 
  • Orange Zest & Chocolate Whoopie Pies 
  • Peanut Butter & Chocolate Whoopie Pies
  • Chocolate Covered Banana Whoopie Pies
  • Chocolate & Ginger Whoopie Pies
  • Salted Caramel filled Chocolate Whoopie Pies
  • Cinnamon & Spice Chocolate Whoopie Pies
whoopie pies side by side with different frosting

More Delicious Chocolate Cookie Recipes


It's Sweet to Share!


  1. OMG those whoopie pies make my mouth water! I am for sure going to try these! Btw thanks for commenting and keepin up with my blog, I get so excited when I get comments on my blog from people other than family, lol. And I will definitly post the glazed lemon bread recipe with blueberry sauce. So check back for the post!


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