Chocolate Whoopie Pies

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These chocolate whoopie pies are the perfect dessert sandwich with two fluffy chocolate cake rounds, with a creamy vanilla buttercream frosting in the middle. Made with buttermilk to keep them moist, and a hint of espresso powder to bring out the chocolate flavor, you won’t be able to resist these whoopie pies!

two chocolate whoopie pies stacked and one with a bite taken out of it leaning next to them


 

When I got my hands on Live Well Bake Often’s cookbook, Live Well Bake Cookies, I started drooling over each page of the cookbook with all the wonderous cookies to make. There were classic cookies of course, and then fun twist on some classic, and others that I just couldn’t resist …like oatmeal cream pies, and a chocolate chip cookie cake that’s perfect for any birthday, and then these chocolate whoopie pies.

Is a whoopie pie a cake? A cookie? A little bit of both? Well I figure since it’s in a cookie book, then we should call these little treats cookies.

But to me, whoopie pies are more cake like in nature with their fluffy cake-like interior. And the fact that they get basically get “frosted” or, well, ok sandwiched with frosting. But seriously I don’t care what you call them. We had a hard time resisting these whoopie pies!! Danielle nailed it on this one.

several whoopie pies in a bowl lined with a linen napkin

What is a whoopie pie?

Growing up in New York, and then moving to Boston I guess I always thought that everyone knew about what the heck whoopie pies were. But perhaps you don’t? And that’s ok. Let me enlighten you. A whoopie pie is basically an individual hand-held chocolate cake sandwich with a perfect buttercream center, and sometimes made with marshmallow fluff.

Although you don’t have to stop at chocolate! You can make all sorts of wonderful whoopie pie flavors. Like these pumpkin whoopie pies from If You Give A Blonde A Kitchen, or these red velvet whoopie pies with cream cheese frosting.

According to Taste of Home, whoopie pies, originate from the New England area, specifically with Maine. Supposedly the first whoopie pies were sold at Labadie’s Bakery in 1925. In fact, the whoopie pie is now the official state treat! But if you’re from Pennsylvania you might say whoopie pies originated there where they originated in Amish kitchen.

What is a whoopie pie made of?

A few notes on the ingredients

Besides gathering all the ingredients above, here are a few special things to take note of:

  • Cocoa powder – You want to make sure to use natural unsweetened cocoa powder and not Dutch process cocoa powder. They have different acidities and will not react the same with your leavening agents, and your whoopie pie texture will not be the same. Or possibly end in a fail!
  • Espresso powder – This ingredient is optional, but coffee will always enhance the flavor of chocolate so I highly recommend.
  • Buttermilk – This whoopie pie recipe calls for buttermilk, which is not the same as thing as milk and you cannot substitute one for the other. If you don’t have any on hand, you can make your own homemade buttermilk version, but the results may vary just slightly.
four whoopie pies lined up in a loaf pan lined with a blue linen napkin

How To Make Chocolate Whoopie Pies

You want to start by sifting together your dry ingredients. Start by sifting together the flour and cocoa powder. This will help get rid of any lumps in the cocoa powder, and help aerate the flour. Then whisk in the baking soda, salt, and espresso powder.

Next you want to cream together your softened butter and sugar. In a large bowl with an electric mixer (hand mixer or stand mixer with paddle attachment), cream together the butter and brown sugar together for 1 to 2 minutes, or until combined. Then Mix in the egg and vanilla until fully combined. Scrap down the bowl as needed. 

butter and sugar creamed together for whoopie pies

Next you want to alternate your dry ingredients and buttermilk. Starting and ending with the dry ingredients, alternate the flour mixture in 3 additions, with the buttermilk.

Mix in until just combined with each addition. Be careful to not overmix at this point. 

chocolate whoopie pie batter in a glass mixing bowl

Next scoop the chocolate whoopie pie batter onto your prepared cookie sheet. I like to line mine with parchment paper. Using a 1 ½-tablespoon cooking scoop, scoop the whoopie pie batter onto the prepared baking sheets, leaving about 2 inches between each one. Use the back of a spoon to smooth out the batter for each whoopie pie before placing them in the oven. 

unbaked chocolate whoopie pies on a parchment lined baking sheet

Then go ahe and bake the chocolate whoopie pies for 11 to 13 minutes, or until the tops of the cookies spring back to the tough. Remove from the oven and cool on the baking sheets for 10 minutes, then transfer the chocolate cookies to a wire rack to cool completely.

baked chocolate whoopie pies on a parchment lined baking sheet

Once the chocolate whoopie pies are cooled, you can go ahead and start assembling them. I made my vanilla buttercream frosting, but you could really use any frosting you like. I like to pair up the whoopie pies according to size. Once the cookies have cooled, pipe on the vanilla frosting onto a flat side of one cookie. I pipe the frosting on, but you can also use an offset spatula. I pipe so there’s a bit of a border, which will leave room for when you “smoosh” the second cookie on top.

hand holding half of a chocolate whoopie pie topped with frosting

Then top with the second cookie and gently press the two cookies together so the frosting then comes to the edge.

hand pressing a chocolate whoopie pie together

Heather’s Baking Tips

  • Sift your dry ingredients together so it helps to aerate the flour and result in a light and fluffy whoopie pie.
  • Room temperature ingredients are important so everything creates a smooth mixture and gets incorporated easily.
  • Use a cookie scoop so you get a perfect round of cake batter that will bake up into perfect whoopie pie rounds.
  • Lightly smooth the tops of each whoopie pie after you’ve scooped them, with a slightly wet finger to ensure they bake up with smooth tops.
  • Once they’re baked, I like to match up the little cakes to see which ones match perfect in size with each other. So each whoopie pie in the end is a perfect little cake.
several chocolate whoopie pies stacked on top of each other on a wire cooling rack

What is a whoopie pie filling made of?

I kept it simple and used my vanilla buttercream frosting recipe but if you prefer a less sweet frosting, then try my Italian meringue buttercream or Ermine frosting. Or you can totally mix things up and try all sorts of fun flavors!

Recipe FAQ’s

How long do whoopie pies stay fresh?

Cover whoopie pies and keep in the fridge for up to one week.

Can I freeze chocolate whoopie pies?

You can freeze whoopie pies for up to 3 months. Wrap each whoopie pie in plastic wrap individually and then transfer to a freezer-safe plastic bag. Thaw at room temperature, unwrapped, before serving.

What is the difference between a moon pie and a whoopie pie?

Whoopie pies have two cake-like rounds with a fluffy vanilla frosting middle in the center. But moon pies have a marshmallow center between two graham cracker like rounds that have been dipped in chocolate.

several whoopie pies on a linen lined basket

More Recipes To Try

Chocolate Whoopie Pies

These chocolate whoopie pies are the perfect dessert sandwich with two fluffy chocolate cake rounds, with a creamy vanilla buttercream frosting in the middle. Made with buttermilk to keep them moist, and a hint of espresso powder to bring out the chocolate flavor, you won't be able to resist these whoopie pies!
5 from 17 votes
Print Pin Rate
Course: Dessert
Cuisine: American
Prep Time: 40 minutes
Cook Time: 13 minutes
Total Time: 53 minutes
Servings: 12 whoopie pies
Calories: 409kcal

Ingredients

For the whoopie pies

  • 2 cups (250 g) all-purpose flour spooned and leveled
  • ½ cup (45 g) natural unsweetened cocoa powder
  • 1 teaspoon baking soda
  • ½ teaspoon instant espresso powder optional
  • ½ teaspoon salt
  • ½ cup (1 stick, 113 g) unsalted butter softened to room temperature
  • 1 cup (200 g) packed light brown sugar
  • 1 large egg at room temperature
  • 1 ½ teaspoons vanilla extract
  • 1 cup (240 ml) buttermilk at room temperature

For the frosting:

  • ¾ cup (1 ½ sticks, 170 g) unsalted butter softened
  • 1 ½ cups (170 g) powdered sugar
  • 1 ½ Tablespoons heavy cream
  • 1 ½ teaspoons vanilla extract

Instructions

To make the whoopie pies

  • Prep oven and pans. Preheat the oven to 350°F (180°C). Line two large baking sheets with parchment paper (or silicone baking mats). Set aside.
  • Combine dry ingredients. In a large mixing bowl, sift together the flour and cocoa powder. Whisk in the baking soda, salt, and espresso powder (if using). Set aside.
  • Cream butter and brown sugar. In a large bowl with an electric mixer (hand mixer or stand mixer with paddle attachment), cream together the butter and brown sugar together for 1 to 2 minutes, or until combined.
  • Add egg and vanilla. Mix in the egg and vanilla until fully combined. Scrape down the bowl as needed.
  • Alternate dry ingredients and buttermilk. Starting and ending with the dry ingredients, alternate the flour mixture in 3 additions, with the buttermilk in 2 additions. Mix in until just combined with each addition. Be careful to not overmix at this point.
  • Scoop the cookies Using a 1 ½-tablespoon cooking scoop, scoop the whoopie pie batter onto the prepared baking sheets, leaving about 2 inches between each one. Use the back of a spoon to smooth out the batter for each whoopie pie before placing them in the oven.
  • Bake. Bake for 11 to 13 minutes, or until the tops of the cookies spring back to the touch. Remove from the oven and cool on the baking sheets for 10 minutes, then transfer the chocolate cookies to a wire rack to cool completely.

To make the frosting

  • Make the frosting. In your stand mixer with a paddle attachment, or in a large mixing bowl with a hand mixer beat the butter for 1 to 2 minutes, until smooth. Add in the powdered sugar, about a ½ cup at a time, mixing on low speed, in each addition until well combined.
  • Add remaining frosting ingredients. Add in the heavy cream and vanilla extract and mix on low speed until combined. Increase speed to medium-high and continue mixing for about 4-5 minutes until light and fluffy.
  • Assemble the whoopie pies. Pair up the whoopie pies according to size. Once the cookies have cooled, pipe on the vanilla frosting onto a flat side of one cookie. I pipe just enough so there's a border of cookie, to give the frosting room when I press the two cookies together. Top with a second cookie to make a “sandwich” by gently pressing the two cookie rounds together and pressing the frosting to the edge. Continue assembling the rest of the whoopie pies.

Notes

  • Storage: Store the whoopie pies in an airtight container in the refrigerator for up to 4 days. Make sure to bring to room temperature before serving so the frosting has time to soften.
  • Freezing: Individually wrap each whoopie pie in a few layers of plastic wrap. I then place them in a large sealable freezer plastic bag. Freeze for up to 3 months. Thaw at room temperature, unwrapped, before serving.
  • Cocoa powder – You want to make sure to use natural unsweetened cocoa powder and not Dutch process cocoa powder. They have different acidities and will not react the same with your leavening agents, and your whoopie pie texture will not be the same. Or possibly end in a fail!
  • Espresso powder – This ingredient is optional, but coffee will always enhance the flavor of chocolate so I highly recommend.
  • Buttermilk – This whoopie pie recipe calls for buttermilk, which is not the same as thing as milk and you cannot substitute one for the other. If you don’t have any on hand, you can make your own homemade buttermilk version, but the results may vary just slightly.

Nutrition

Calories: 409kcal | Carbohydrates: 52g | Protein: 4g | Fat: 22g | Saturated Fat: 13g | Trans Fat: 1g | Cholesterol: 69mg | Sodium: 224mg | Potassium: 144mg | Fiber: 2g | Sugar: 34g | Vitamin A: 671IU | Vitamin C: 1mg | Calcium: 55mg | Iron: 2mg
Tried this Recipe? Pin it for Later!Mention @BostonGirlBakes or tag #BostonGirlBakes!


 

30 Comments

  1. Lisa Sollenberger says:

    Do you have a peanut butter icing recipe that would go good with these ? Making some for a wedding but they want peanut butter icing.

  2. 5 stars
    Whoopie pies are the best! Loved how these turned out – so soft and chocolatey and delicious!

    1. Thanks Amy! Glad you loved them!

  3. 5 stars
    I honestly cannot even remember the last time I had a whoopie pie. These always remind me of my childhood…these look delicious! I have to make these ASAP!

    1. Right? Brings you back when you bite into one!

  4. Really good. I added about 2.5 cups of powdered sugar and a bit more cream to the frosting. Thanks for sharing.

    1. Glad you loved them Kristen 🙂

  5. Amanda Mason says:

    5 stars
    The kids really enjoyed these and they were so easy to make! Thanks for a great recipe! We will be making them again!

    1. Wonderful Amanda..glad they were a hit!

  6. Dennis Littley says:

    5 stars
    This was my first time making whoopie pies and your recipe came out great!

    1. That’s wonderful to hear Dennis!

  7. Veronika Sykorova says:

    5 stars
    Whoopie Pies will always be my favorite dessert. I tried these last nigh and everyone loved them! They disappeared so fast , we only have three left!

    1. Glad they were a hit 🙂

  8. 5 stars
    I’m so glad you used vanilla buttercream frosting for this recipe. Such an amazing combination with the chocolate! This recipe does NOT disappoint!

    1. It’s a great pairing 🙂 glad you loved them!

  9. 5 stars
    I haven’t made whoopie pies in AGES!! This needs to change, making these ASAP! Thanks so much for the recipe 🙂

    1. They’re such a classic 🙂 enjoy!

  10. 5 stars
    These chocolate whoopie pies are layers of YUM! The cake was so soft and fluffy and the frosting added another layer of sweet flavor.

  11. Sandhya Ramakrishnan says:

    5 stars
    My boys love whoopie pies but I have never been bold enough to give it a try. Thanks for the detailed recipe. I have it printed out and I can’t wait to give it a try.

  12. 5 stars
    I love whoopie pies and these look scrumptious! I love how easy they are to make.

  13. 5 stars
    You weren’t lying when you said the espresso powder brings out more of the chocolate flavor. These whoopie pies were a hit with my entire family.

    1. Taylor Smith says:

      The espresso powder just adds that little something extra, doesn’t it?

  14. 5 stars
    My kids went crazy over these. Can’t wait to make again! Thank you. 🙂

  15. 5 stars
    These are so good and easy to make! Even for someone like me who doesn’t bake often and isn’t necessarily good at it, haha. Will definitely be making these again.

  16. 5 stars
    WOW! I always wanted to make sandwiched cookies, and this is my chance! Well, I tried your recipe today, and it turned out to become my new favorite. Thanks for the detailed instructions!!

    1. Taylor Smith says:

      You’re so welcome. I’m glad you enjoyed the recipe!

  17. 5 stars
    Yum!! These whoopie pies brought me back to my childhood! They were sweet and fluffy and super easy to make!

    1. Taylor Smith says:

      Yes, we are definitely throwing it back with this recipe haha.

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