Chocolate Whoopie Pies With Buttercream Filling

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Check out these chocolate whoopie pies with cherries! The perfect cherry and chocolate duo is filled with a silky smooth buttercream filling. This homemade whoopie pie recipe is such a treat. The studs of cherries really transform the flavor of these cookies!

Whoopie Pies are something we don’t have too often. But when we do this cherry Garcia recipe, here is one we reach for. There is something special when maraschino cherries and chocolate join forces.

Want more delicious whoopie pie recipes to try out?  If you loved this recipe and you’d like some more whoopie pie recipes, check out this collection of 19 easy whoopie pie recipes. Or, for something a little different, make a pumpkin whoopie pie complete with a cream cheese frosting.

Still have the urge to make more chocolate recipes? Then you could try some simple heart shaped brownies  with white chocolate frosting.

Why You’ll Love This Recipe

• Simple and Fun to Make: This recipe guides you through the delightful process of creating the best whoopie pies from scratch, making it a fun baking project for any skill level.
• Unique Flavor Combination: The combination of juicy cherries and rich chocolate offers a taste experience that’s both unique and satisfying.
• Perfect for Any Occasion: Whether you’re preparing for a holiday, a special event, or just want to treat yourself, these chocolate whoopie pies with buttercream filling are sure to impress.
• Customizable: Feel free to experiment by adding different types of fruit or even using various fillings to make these whoopie pies your own.

What Are Whoopie Pies?

Whoopie pies might sound like a whimsical name for a dessert, but behind it lies a treat beloved in many areas for its soft, cake-like texture and rich, creamy filling. Essentially, whoopie pies are made of two round, mound-shaped pieces of cake, typically chocolate-flavored, sandwiched around a sweet, fluffy filling. This filling often consists of buttercream, marshmallow cream, or flavored frostings that complement the cake. 

Originating from the Amish tradition as a way to use leftover cake batter, whoopie pies have gained widespread popularity and now come in various flavors besides the classic chocolate. While sounding simple, the texture and taste balance between the moist cake and the creamy filling make whoopie pies a surprisingly sophisticated and satisfying dessert.

What’s In This Chocolate Whoopie Pies Recipe?

• Flour: The foundation of our whoopie pies, flour provides the necessary structure to hold all the delicious flavors together. Opt for all-purpose flour to achieve a soft, cake-like texture.
• Baking Soda: Acting as a leavening agent, baking soda ensures that our whoopie pies rise to perfection, giving them their characteristic fluffy texture.
• Salt: A pinch of salt is crucial in baking to enhance the overall flavors of the other ingredients, making the chocolate and cherries in these whoopie pies pop.
• Sweet Cream Butter: The butter adds richness and moisture to both the whoopie pie cakes and the buttercream filling, ensuring each bite is decadently smooth.
• Egg: The egg binds the ingredients together, contributing to the cake’s structure and moistness.
• Brown Sugar: Using brown sugar not only sweetens the recipe but adds a hint of caramelized flavor, complementing the chocolate and cherries beautifully.
• Vanilla: A splash of vanilla extract enhances the sweetness and adds depth to the overall flavor profile of the whoopie pies.
• Milk: Milk softens the batter, contributing to the tender texture of the cake, and makes the buttercream filling lusciously creamy.
• Maraschino Cherries: Chopped maraschino cherries add a burst of sweet, tangy flavor and a pop of color to every bite, making the whoopie pies visually appealing and deliciously unique.
• Chocolate Chips: Melted into the batter and the filling, chocolate chips intensify the chocolatey goodness, making these whoopie pies a dream come true for chocolate lovers.
• Heavy Cream: Used in the filling, heavy cream whips up beautifully to create a light, fluffy texture that contrasts delightfully with the dense cake.
• Powdered Sugar: It sweetens and thickens the buttercream filling to the perfect consistency, ensuring it holds its shape while sandwiched between the cake layers.

The complete list of ingredients, quantities, and instructions can be found in the printable recipe card below.

Substitutions and Variations

• Gluten-Free Flour: For those with gluten sensitivities, you can easily substitute the all-purpose flour with your favorite gluten-free blend to make these treats accessible for everyone to enjoy.
• Alternative Sweeteners: If you’re watching your sugar intake, consider swapping the brown sugar for coconut sugar or a granulated sugar alternative that measures like sugar.
• Dairy-Free Options: To accommodate dairy-free preferences, use margarine or a plant-based butter substitute instead of sweet cream butter and opt for almond milk or oat milk instead of dairy milk in the cake and frosting.
• Add Nuts: For an added crunch and nutty flavor, consider folding chopped walnuts or pecans into the batter.
• Fruit Variations: While maraschino cherries offer a unique flavor and pop of color, don’t hesitate to experiment with other fruits, such as raspberries, blueberries, or even candied orange peel, for a different twist.
• Dark Chocolate: For a richer, more intense chocolate flavor, substitute the chocolate chips with dark chocolate or add cocoa powder to the batter.
• Spice It Up: Introduce spices such as cinnamon, nutmeg, or even a pinch of cayenne pepper to the batter for an unexpected warmth and depth of flavor.
• Coffee Flavored: To enhance the chocolate flavor further, add a teaspoon of espresso powder to the batter or the filling.

How to Make Chocolate Cherry Whoopie Pies (step-by-step directions)

1. Preheat your oven and prepare your whoopie pie pan as per the instructions.
2. Combine all the dry ingredients in a large bowl and set aside after mixing well.
3. Use an electric hand mixer or stand mixer to blend the wet ingredients until thoroughly mixed.
4. Gradually alternate adding the dry ingredients with milk to the wet mixture, ensuring to mix well and scrape down the sides of the bowl.
5. Fold in the chocolate chips and chopped maraschino cherries into the batter until evenly distributed.
6. Spoon the whoopie pie batter into the slots of the whoopie pie pan.
7. Bake according to the given instructions.
8. Once baked, remove the whoopie pies from the oven and allow them to cool on a cooling rack before proceeding.
9. Prepare the homemade frosting by mixing the ingredients until smooth.
10. Pipe a ring of the freshly made frosting onto the center of one cookie, then top it with another cookie to complete your whoopie pie. (Photos 1, 2 & 3)

Recipe Tips

• Don’t Overmix the Batter: To ensure your whoopie pies remain light and fluffy, mix the batter until just combined. Overmixing can lead to tough cakes.
• Room Temperature Ingredients: For the best results, ensure all your ingredients are at room temperature before starting. This helps to achieve a smoother batter and frosting.
• Checking for Doneness: Insert a toothpick into the center of a cake to check if it’s done. If it comes out clean, your whoopie pies are ready to be taken out of the oven.
• Consistent Size: Use a cookie scoop or a measuring spoon to ensure all your whoopie pies are the same size. This not only helps them bake evenly but also makes assembling them easier.
• Cool Completely Before Filling: Allow the cakes to cool completely before adding the frosting. Warm cakes can cause the frosting to melt and make a mess.
• Get Creative with Frosting: Use a piping bag with a star tip to add an elegant touch to your whoopie pies, or simply spread the frosting with a knife for a rustic look.
• Test Your Baking Soda: Make sure your baking soda is active for the cakes to rise properly. You can test it by adding a little vinegar; if it bubbles, it’s good to use.

Storing Tips 

I like to take the chocolate chip cookie whoopie pies and wrap them in plastic wrap to help ensure they do not dry out as fast. Then for the frosting, I find that storing at room temperature works. But if you store in the fridge in an airtight container they will store for 2-3 days longer than normal.

Go right ahead and freeze as many as you like. Place each one in a freezer container and freeze it for 3-4 months. Then, you can thaw on the counter or in the fridge for a slower thaw.

Serving Suggestions

For a classic pairing, serve the pies with a glass of cold milk – the creaminess of the milk complements the richness of the chocolate and cherries beautifully. If you’re looking for something warmer, a cup of coffee or espresso can accent the chocolate flavor, making for an indulgent treat perfect for a cozy gathering.

For those who enjoy a bit of contrast, a scoop of vanilla or cherry ice cream alongside the whoopie pies could offer a delightful play of textures and temperatures. 

Lastly, for an afternoon tea or brunch, these whoopie pies can be beautifully arranged on a platter with other recipes such as marshmallow fruit salad or single serve mini cherry cheesecakes that everyone will enjoy.

Recipe FAQs

More Desserts You’ll Love

• Godiva Chocolate Whoopie Pies
• Pumpkin Whoopie Pies
• Chocolate Chip Whoopie Pies
• Dessert Burger Whoopie Pies
• See all of our delicious dessert recipes!

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