Sourdough Chocolate Peppermint Whoopie Pies

These festive Sourdough Chocolate Peppermint Whoopie Pies are made with two chocolate and fudgy cake-like cookies that sandwich peppermint buttercream and rolled in crushed peppermint.

My sourdough pumpkin whoopie pies were so popular this fall, that I had multiple requests to make a chocolate and holiday version. I came up with these soft cake-like sandwich cookies that are full of chocolate and peppermint flavor and made with sourdough discard.

The chocolate whoopie pies encase a velvety and simple peppermint American buttercream, elegantly finished with a roll of crushed peppermint (or candy canes) for a delightful crunch and quintessential red-and-white peppermint candy allure.

Experience the joy of baking these timeless New England treats – a perfect addition to festive gatherings, holiday parties, or Christmas celebrations! My recipe walks you through each step of the process, including lots of detailed tips and photos.

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What are Whoopie Pies?

Whoopie pies are soft sandwich cookies made with a cake-like batter. The soft cakes (they’re more cake-like than cookies) surround a sweet filling made of buttercream, cream cheese frosting, marshmallow fluff, or even my less-sweet Sourdough Frosting.

Whoopie pies are a New England delicacy with some contentious origins among New England states. Most sources point to their creation in Maine, where it was named the official state treat in 2011.

Whoopie pies are also popular among Pennsylvania Amish communities, where they’re made from leftover cake batter. In the Pittsburgh area, they’re called Gobs.

Whoopie pies are typically chocolate-flavored with a white vanilla frosting filling that resembles a large Oreo cookie, just like these cookies before being rolled in peppermint.

You’ll increasingly find whoopie pies in many bakeries across the United States with various flavors and unique fillings as they grow in popularity.

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👍 Why You’ll Love This Recipe

• Soft and rich chocolate cakes:
  • These sourdough chocolate cakes boast an indulgent cocoa richness. Enhanced with Dutch-process cocoa powder and, if desired, a hint of espresso powder for an intensified chocolate experience.
  • If you’re a chocolate fan, you’ll love my Chocolate Raspberry Sourdough Biscotti, my Sourdough Pumpkin Chocolate Chip Bread, or my Sourdough Discard Chocolate Chip Cookies.
• Can make with any filling:
  • The peppermint American buttercream is easy to make and isn’t so strong that it tastes like toothpaste! The mint here is just enough to pique your interest, and the peppermint candy adds a nice crunch to the outside.
  • However, you could use another filling like my Sourdough Frosting, the brown butter cream cheese frosting on my Sourdough Cinnamon Rolls, or any flavor to fill these too.
• It’s an easy, versatile recipe:
  • There’s no fermenting since the whoopie pies use sourdough discard. The baking soda activates with buttermilk, and the egg helps them rise. That way, the pies rise in the oven quickly.
• Whoopie Pies stores easily:
  • Whoopie pies store well, which makes them great to make ahead, gift, or travel with.
  • You can freeze the soft cookies ahead of time and easily wrap to store for months in the freezer.
• No oil:
  • I only use butter in this recipe as the fat and don’t use vegetable oil. Like my Sourdough Zucchini Bread and Sourdough Banana Bread recipes, I try to avoid using too much vegetable oil in recipes because it doesn’t add any flavor!
  • Instead, the melted butter adds richness, tenderness, and flavor.

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🔍 Troubleshooting Tips

• Don’t overmix the batter
  • Overmixing leads to gluten development, which will create a tough batter. Like cake or pastry, you want to limit the mixing here so you get tender and soft cookies.
• Sift the dry ingredients
  • Prevent large lumps and ensure thorough mixing by sifting dry ingredients into the bowl of wet ones. While not typically emphasized in baking, it’s especially useful for cocoa powder, known to clump more than other ingredients.
• Use espresso powder to bring out the chocolate flavor
  • A trick I learned a long time ago from Ina Garten is to add instant coffee or espresso powder to chocolate desserts to help bring out the chocolate flavor. It’s optional, but a nice touch that enhances the chocolate flavor!
• Refrigerate the whoopie pie batter before baking
  • I highly recommend refrigerating the whoopie pie batter before baking so that the whoopie pies don’t flatten too much. If the batter is warm, they tend to flatten some when they bake.
  • Refrigerating the batter while the oven preheats or up to overnight will help the whoopie pies bake taller.
• Let the whoopie pie cakes cool before filling
  • Buttercream is…well, mostly butter…so if you fill the whoopie pies while they’re warm, the filling will melt out. Let the whoopie pies cool completely before filling them.
  • Plus, the whoopie pies will crumble and easily break apart while still warm.

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🛠 Tools Needed:

Click the links below for my tool recommendations.

• Baking Scale
  • Weighing ingredients is much more accurate than measuring by volume. Discard recipes tend to be more forgiving than bread recipes though, so I do provide standard measurements as well.
• Sheet Pans
  • This recipe makes about 12 large sourdough whoopie pies, or 24 individual cakes. You can easily double the batter to make more.
  • I can fit all 24 scoops of batter onto two large baking sheets (about 2 TBS each), separated by a couple of inches. If you don’t have large baking sheets, you’ll need to bake less at a time. Just make sure they aren’t too close together or they’ll bake into each other!
• Whisk
• Spatula, for scraping the sides of the bowl.
• Cookie or Ice Cream Scoop, optional but helpful
  • For even-sized and round whoopie pies, it’s helpful to use a 2 TBS cookie scoop or small ice cream scoop.
  • However, it’s not 100% necessary and you can certainly use a round tablespoon.
• Stand Mixer or hand mixer, optional but helpful for the buttercream
  • You can make buttercream by hand using an electric hand mixer. However, a stand mixer will really make the process a lot easier!
• Piping Bag, optional but helpful
  • I like using a piping bag with a round tip to pipe the peppermint buttercream. It allows for a little more control when adding the filling so that you don’t overfill the whoopie pies. However, you can easily use a small cookie scoop or spoon to get the job done.
  • For a crafty piping bag, use a plastic ziplock bag and cut off one of the corners!

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🛒 Ingredients Needed:

Click on the links below for my favorite ingredient recommendations. Ingredient substitutions are also listed below.

🍫 Sourdough Chocolate Whoopie Pies

• All-purpose Flour
  • This recipe has only a cup and a half of flour, not including the sourdough discard. All-purpose works best, but you’re welcome to substitute some of it with whole wheat flour if you’d like.
• Baking Soda
  • You only need baking soda in this recipe, as it activates with the acidic buttermilk and sourdough discard.
  • Both baking powder and soda go bad over time. Learn how to test yours here.
• Salt
• Dutch-process cocoa powder
  • Dutch-process cocoa powder is darker in color, richer, and less acidic than natural cocoa powder.
  • If you don’t have or can’t find, you can substitute it in this recipe with natural unsweetened cocoa powder (such as Hershey’s).
• Espresso powder (optional)
  • Coffee brings out more chocolate flavor. I use espresso powder, but you could easily leave out or substitute with instant coffee granules.
• Light Brown Sugar
  • Brown sugar provides sweetness and also adds more moisture and flavor from the added molasses, just like in this Sourdough Anadama Bread.
• Egg
• Sourdough Discard
  • If you don’t have an active sourdough starter, learn how to make one in a week following my how-to guide. See my top sourdough starter tips here.
• Buttermilk
  • The discard and buttermilk are acidic ingredients that help activate baking soda and provide a more moist and tender whoopie pies.
  • Don’t substitute the buttermilk with another milk here! If you have to, you can use kefir or thinned out yogurt or sour cream.
• Vanilla Extract
• Unsalted Butter, melted
  • There’s no oil in this recipe. The melted butter adds richness and needed fat for moisture.

Peppermint Buttercream

• Softened Unsalted Butter
  • Let your butter sit out while you make the whoopie pie cakes so that it will soften. Too warm and the buttercream will melt; too cold and the buttercream will have chunks of butter instead of being silky smooth.
• Powdered Sugar
• Peppermint Extract
  • You can leave it out and substitute it with vanilla extract or another flavoring.
• Kosher Salt
  • Just a small pinch to bring out the flavors a little more.
• Crushed Peppermint Candy
  • I use candy canes (*festive*), but you could use any other hard red and white peppermint candy.
  • I crush it in a ziplock bag with a rolling pin into a mix of small pieces.

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👨‍🍳 How to Make Sourdough Chocolate Peppermint Whoopie Pies

Follow this visual and detailed recipe guide as you make these delicious sourdough chocolate whoopie pies.

If you’ve made my Sourdough Pumpkin Whoopie Pies, this recipe and process is almost identical, except they make slightly larger whoopie pies and more buttercream.

1. Mix the Dry Ingredients

Whisk the dry ingredients together in a small bowl, including:

• 180 grams (1 ½ cups) of all-purpose flour
• 1 ½ teaspoons of baking soda
• ½ teaspoon of salt
• 1 teaspoon of espresso powder (optional)
• 57 grams (⅔ cup) of Dutch-process cocoa powder

Set aside.

2. Mix the Wet Ingredients

In a large mixing bowl, melt 113 grams (½ cup, one stick) of unsalted butter and let it cool for a few minutes at room temperature.

Then, whisk in the following wet ingredients:

• 200 grams of light brown sugar (1 cup)
• 1 egg
• 120 grams (½ cup) of sourdough discard (½ cup)
• 227 grams (1 cup) of buttermilk at room temperature
• 1 teaspoon of vanilla extract

3. Mix the Chocolate Whoopie Pie Batter

Sift the dry ingredients to the bowl of wet ingredients and slowly mix until mostly combined. It’s okay if the batter is a little lumpy, but the sifting should help prevent too many lumps.

Only mix until no flour specks remain to avoid overmixing.

4. Preheat the Oven and Refrigerate the Batter

Preheat the oven to 350ºF (177ºC) and place two oven racks in the top third and bottom thirds of the oven.

For best results, refrigerate the whoopie pie batter while you preheat the oven.

This is especially helpful if the batter seems runny or too warm. Refrigerating will make scooping easier and will help the whoopie pies not flatten as much during baking.

Baking a cooled batter is a similar technique to making flaky and tall pastries such as biscuits, scones, pie crust, or shortcakes. The cooled batter will hold its shape better.

5. Bake

Prepare the baking sheets with parchment paper or silicone baking mats to prevent sticking.

Use a 2 TBS cookie scoop or a large spoon to scoop mounds of round whoopie pie batter onto the sheets, with a couple of inches in between each scoop.

I can fit 12 whoopie pies onto each sheet in rows of 4×3 using large sheet pans. I bake two pans at a time because my oven bakes evenly.

However, if you have smaller sheet pans, fit as many as you can at a time. Don’t bake them too close together or you risk the pies baking into each other.

Bake the whoopie pies at 350ºF (177ºC) for about 14-15 minutes. Rotate the pans halfway through if your oven bakes unevenly.

Bake the whoopie pies until a toothpick inserted into the middle comes out clean and the tops have a matte appearance.

Cool in the pans for a couple of minutes and then use an offset or fish spatula to transfer the cakes to cool on a wire rack completely. If you don’t transfer the cakes, the bottoms tend to stick some.

6. Make the Peppermint Buttercream

Add two sticks of softened unsalted butter (226 grams, 1 cup) and a pinch of salt to the stand mixer bowl with a paddle attachment.

Alternatively, make the buttercream in a mixing bowl using a hand mixer. Whisking by hand is possible, but more challenging, especially with this large amount of buttercream.

Begin mixing on low speed and slowly increase to medium-high until the butter is soft and fluffy, a few minutes. Scrape the sides as needed.

Turn off the mixer and dump in 2 cups (240 grams) of powdered sugar. Powdered sugar will go everywhere if you immediately turn on the mixer, so I like to cover the bowl with a dish towel as I start mixing.

Pulse the mixture slowly and start mixing at the lowest speed. Slowly increase to medium speed to mix a few minutes and then add the remaining 2 cups (240 grams) of powdered sugar and repeat mixing until completely incorporated and thee buttercream is silky smooth.

While mixing, drizzle in ½ teaspoon of peppermint extract or to taste. The extract can be strong and you don’t want it to taste like toothpaste!

If the buttercream seems stiff or dry, drizzle in 1-2 tablespoons of whole milk or heavy cream to loosen it up some.

Transfer the peppermint buttercream to a piping bag or leave it in the bowl.

7. Assemble

I like to use a piping bag to add the filling to the whoopie pies, but you’re welcome to spoon the filling onto the pies. If the pies are too soft or sticky, refrigerate them before filling.

Pipe about 3 tablespoons of peppermint buttercream to a flat side or bottom of half of the whoopie pies. I fill these to almost to the edges so I’ll be able to roll them in peppermint candy easily.

Then, place the other half of the whoopie pies on top to sandwich the cookies.

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How to Store

Whoopie pies store well, and you can make both the pies and the fillings separately and in advance. This is very helpful if you’re planning to make whoopie pies for a gathering, party, or to have an dessert for later.

You can make the peppermint buttercream and store it in a sealed container in the refrigerator for up to a week in advance. Let it sit at room temperature for about 30 minutes and remix slightly before filling.

For the whoopie pies, you can make them a couple of days in advance and store them wrapped well in plastic wrap or an airtight container in the refrigerator.

The pies do get more sticky over time and if left at room temperature, tend to take on more moisture if it’s humid.

Can I Freeze?

I don’t recommend freezing assembled whoopie pies as the buttercream tends not to thaw well.

However, the individual whoopie pie cakes can be frozen on a sheet pan for at least an hour and then stored in freezer-safe bags so they don’t stick together for a few months.

Thaw the whoopie pies overnight in the refrigerator before assembling.

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❓FAQs:

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