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Chocolate Peppermint Whoopie Pies

Love chocolate and peppermint? You'll love these sweet, delicate Chocolate Peppermint Whoopie Pies!

For this month’s cookie of the month, I feel like I’m cheating a little bit. Whoopie pies always make me think of cookies. They look and eat like a cookie, but they have a consistency similar to cake. To confuse the situation further, they’re called pies. Go figure.

Regardless of the technicalities of their classification, I assure you they are delicious. These beauties consist of dark chocolate, cake-like cookies filled with a peppermint cream cheese frosting.

Peppermint and chocolate are a perfect pair in these lovely, delicate, delicious Chocolate Peppermint Whoopie Pies! - Bake or Break

The recipe for these comes to us from One Girl Cookies, a lovely bakery with a very handy (and dangerous!) location in my neighborhood. They always have whoopie pies tempting me from their display case. Their usual chocolate whoopie pies have traditional cream cheese frosting, but this peppermint variety is a holiday favorite in their cookbook.

I normally hesitate to bake anything that requires piping batter or frosting. It’s just not my favorite thing. And truth be told, I’m not very good at it. If you don’t take away anything else from this, here’s what I want you to know. Even with my mediocre piping skills, these little guys always turn out beautifully. They are very forgiving. Believe me, they don’t go into the oven looking nearly as good as the finished product.

Through some sort of baking magic, these cookies turn from lumpy, misshapen blobs into beautiful cookies. Then just fill them with frosting, whether it be this peppermint frosting or your favorite variety. When you serve these to your friends, you’ll be a baking rock star!

These cookies are my contribution to Cookie of the Month, a monthly group of cookie recipes from some of my blogging friends and me. This month’s theme is mint. Be sure to visit these ladies’ blogs to see their mint cookie creations!

Catch up with the previous Cookies of the Month with Cherry-White Chocolate Oatmeal Cookies and Fudgy Kahlua Brownie Cookies.

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Chocolate Peppermint Whoopie Pies

Yield 24 whoopie pies
Prep Time 25 minutes
Cook Time 10 minutes
Total Time 35 minutes

Peppermint and chocolate are a perfect pair in these lovely, delicate, delicious Chocolate Peppermint Whoopie Pies!

Love chocolate and peppermint? You'll love these sweet, delicate Chocolate Peppermint Whoopie Pies!

Ingredients

For the cakes/cookies:

  • 2 cups all-purpose flour
  • 1/2 cup Dutch-processed cocoa powder, sifted
  • 3/4 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1/2 cup granulated sugar
  • 1/2 cup firmly packed light brown sugar
  • 1/2 cup plain full-fat yogurt*
  • 1/3 cup canola oil
  • 3 large eggs
  • 1 teaspoon vanilla extract

For the filling:

  • 4 ounces cream cheese, softened
  • 5 tablespoons unsalted butter, softened
  • 1/2 teaspoon peppermint extract
  • 1/8 teaspoon salt
  • 2 & 1/2 to 3 cups confectioners' sugar, sifted**

Instructions

To make the cakes/cookies:

  1. Whisk together the flour, cocoa powder, baking soda, and salt. Set aside.
  2. Using an electric mixer on medium speed, beat the sugar, brown sugar, yogurt , oil, eggs, and vanilla until thoroughly combined and smooth (about 3 minutes).
  3. Reduce the mixer speed to low. Gradually add the flour mixture and mix just until combined. Refrigerate the batter for 30 minutes.
  4. Preheat oven to 350°. Line a baking sheet with parchment paper.
  5. Using a pastry bag with a large plain tip or a plastic bag with the corner snipped, hold the bag vertically and very close to the parchment paper, and pipe the batter in 2-inch circles onto the prepared pan. Leave about 1 & 1/2 inches between each.
  6. Bake for 10 minutes, or until the centers spring back when touched. Repeat with remaining batter, baking one sheet at a time. Cool the whoopie pies completely.

To make the filling:

  1. Using an electric mixer on medium speed, beat the cream cheese and butter until light and fluffy. Add the peppermint and salt, and mix well.
  2. Reduce the mixer speed to low. Gradually add the confectioners' sugar, and mix well.

To assemble the whoopie pies:

  1. Turn half of the whoopie pies so that the bottoms face upward.
  2. Pipe or spread 1 to 1 & 1/2 tablespoons of filling on each.
  3. Top with the remaining whoopie pies.

Notes

*Confession: I tend to use the yogurt I always have on-hand, which is a non-fat vanilla yogurt. It works just fine.

**I like my cream cheese frosting a little less sweet than most. If you like yours on the sweeter side, use the full 3 cups of confectioners' sugar. 

Recipe very slightly adapted from One Girl Cookies: Recipes for Cakes, Cupcakes, Whoopie Pies, and Cookies from Brooklyn's Beloved Bakery.

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    25 Comments on “Chocolate Peppermint Whoopie Pies”

  1. Those sound terrific! You can’t go wrong with peppermint + chocolate ๐Ÿ™‚

  2. These look so doggone perfect! I’ve never tried to make them, but sure want to soon after seeing these! Yum Girl and Kelli!

  3. I love whoopie pies! They turned out so pretty! I bet they are amazing with the mint flavor.
    Blessings,
    Nici

  4. Whoopie pies are the best! And yours look perfect. ๐Ÿ™‚

  5. Those look quite delicious, Jennifer and yours look so perfect!

  6. Oh I definitely think whoopie pies count as cookies! Especially these, they look divine!

  7. These are beautiful!! One of my favorite flavor combos!

  8. ohhhh I miss whoopie pies! yours look superb! ๐Ÿ˜€

  9. I simply adore whoopie pies. I have never made them but boy, you have made me want to try.

  10. I love whoopie pies! These look fantastic!

  11. These look amazing. I have never made my own whoopie pies, but this recipe makes me want to change that!

  12. Whoopie Pies are Peppermint has GOT to be a heavenly combination! I might try this one with the next party we have (just so I don’t eat them all myself ๐Ÿ˜‰ )

  13. Cake, pie or cookie, these look delicious!

  14. One of my favourite combos – Chocolate & Peppermint! I’m not great at piping either, so these are right up my alley!

  15. My whole family loves chocolate and peppermint together. These look wonderful. We are definitely giving them a try. ๐Ÿ™‚

  16. How do you get your cookies to look so beautiful?! Chocolate and peppermint is one of my favorite combinations – these could send me straight to heaven.

  17. Whoopie Pies are one of my favorite treats out there and I love the idea of a peppermint kick! Thanks so much! xo Nic (PSโ€ฆI am right there with you the “piping” trepidations!)

  18. Love these…I don’t know that I ever ate a whoopie pie as a kid, but I will as an adult. The peppermint sounds like a perfect touch!

  19. I’m glad I’m not the only one who can’t quite figure out how to classify a whoopie pie. Whatever they are, though, they’re delicious! Love how pretty these turned out, despite sad piping skills… given that mine are probably even worse, it’s very reassuring to know that they’ll magically turn out. ๐Ÿ™‚

  20. You know i have never tried these before, I think that I will give them a go and see how it pans out. (excuse the pun !!).

  21. It’s been a very long time since I’ve made whoopie pies. This mint version sounds amazing.

  22. I classify whoopie pies as cookies also, so I think you’re in the clear. Love this flavor! We are chocolate + peppermint addicts.

  23. I am a big fan of chocolate. Your recipe looks great. I will try soon.

  24. These were great! After reading through the reviews, I planned on serving these right from the freezer so I actually mixed a little bit of cool whip into the filling . I also substituted just a little of butter for the shortening. The cookies were great, I didn’t think they were lacking in flavor at all. Thanks for your sharing!

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