Chocolate Covered Strawberry Whoopie Pies

Decadent Chocolate Strawberry Whoopie Pies: The Ultimate Easy Recipe

Prepare to fall in love with these incredibly easy Chocolate Strawberry Whoopie Pies! Crafted effortlessly from a convenient Devil’s food cake mix, these delightful treats feature soft, rich chocolate cake shells piped into charming heart shapes (or classic circles) and generously filled with a luscious strawberry buttercream, made vibrant with real strawberry jam. Perfect for Valentine’s Day, anniversaries, or any moment you crave a touch of chocolate and strawberry sweetness in your life.

Heart Shaped Chocolate Strawberry Whoopie Pies on a white plate with fresh strawberries

Celebrate Love (and Dessert!) with These Irresistible Treats

Can you feel the love in the air? Valentine’s Day is just around the corner, and what better way to embrace the spirit of romance and indulgence than with these adorable Heart Shaped Chocolate Strawberry Whoopie Pies? While some might dismiss Valentine’s as a “Hallmark Holiday,” I see it as a wonderful excuse to spread joy and enjoy something truly special. For me, that means breaking out the pink and red decorations, perhaps some heart-shaped doilies, and definitely baking a batch of these exquisite whoopie pies!

These aren’t just for February 14th, though. Their delightful flavor and charming appearance make them suitable for any celebration – a birthday, an anniversary, a special family gathering, or simply a treat to brighten an ordinary Tuesday. There’s something inherently comforting and celebratory about a homemade dessert, especially when it’s as visually appealing and delicious as these whoopie pies.

Close up of a Chocolate Strawberry Whoopie Pie with a bite taken out, showing the pink filling

The Timeless Pairing of Chocolate and Strawberry

In my humble opinion, there can never be too much chocolate in the world. Numerous studies have consistently shown that chocolate can genuinely elevate your mood. Darker chocolates, in particular, contain compounds that stimulate endorphins – those wonderful chemicals your brain releases after a good laugh or an invigorating workout. In today’s fast-paced world, a little extra happiness is something we could all use, right?

These whoopie pies take that happiness a step further by introducing the vibrant freshness of strawberries. The combination of chocolate and strawberries is a classic for a reason – they complement each other perfectly, creating a flavor profile that is both rich and refreshing. Just like Bert and Ernie, some things are simply better together. The deep, intense flavor of chocolate cake pairs beautifully with the sweet, slightly tart notes of strawberry, making each bite an unforgettable experience. It’s a sophisticated yet comforting blend that appeals to almost everyone.

Chocolate Strawberry Whoopie Pies with powdered sugar and fresh strawberries scattered around

Versatility in Shape: Heart-Shaped or Classic Round?

While my mind is currently immersed in all things Valentine’s, lending these whoopie pies their charming heart shape, remember that creativity knows no bounds in the kitchen! You are absolutely welcome to make them round. Opting for a classic circular shape can make the piping process even quicker and easier, especially if you’re making a large batch or if you prefer a more traditional look. Rest assured, whether they’re shaped like hearts or perfect circles, these chocolate whoopie pies with strawberry cream filling will taste just as incredible. The soft, pillowy chocolate cake and the creamy, fruity filling are the stars of the show, regardless of their form.

A collage image promoting 'Pin Them!!' for Chocolate Strawberry Whoopie Pies

Save This Easy Chocolate Strawberry Whoopie Pie Recipe!

Excited to try your hand at these delightful treats? Don’t let this fantastic and easy Chocolate Strawberry Whoopie Pie recipe slip away! Make sure to save it so you can whip up a batch whenever a craving strikes or a special occasion calls for something sweet and homemade. It’s a recipe you’ll want to revisit again and again.

Simple Ingredients for Heavenly Whoopie Pies

One of the best aspects of this whoopie pie recipe is its simplicity, largely thanks to a secret weapon: a Devil’s Food cake mix! Using a cake mix cuts down on prep time significantly without sacrificing flavor or texture. This means less measuring and fewer bowls, allowing you to get to the delicious part even faster. Gather these basic ingredients for the moist and tender chocolate cake shells:

Ingredients for Chocolate Whoopie Pie cakes including Devil's food cake mix, eggs, vegetable oil, and vanilla extract

  • Devils Food cake mix (your favorite brand)
  • Large eggs (at room temperature for best mixing)
  • Vegetable oil
  • Vanilla extract (enhances the chocolate flavor beautifully)

Baking Your Perfect Chocolate Whoopie Pie Shells

Creating the foundation for these incredible whoopie pies is straightforward. Follow these steps for perfectly baked, fluffy chocolate cake halves:

Mixing ingredients for Chocolate Whoopie Pies in a stand mixer

  • Preheat your oven to 350 degrees F (175 degrees C). Prepare your cookie sheets by lining them with parchment paper. This prevents sticking and makes for easy cleanup.
  • In a large mixing bowl, combine the cake mix, eggs, vegetable oil, and vanilla extract. Beat these ingredients with an electric mixer until they are just incorporated. Then, increase the speed to medium and beat for an additional 2 minutes. This ensures a smooth batter and a light texture.
  • For heart-shaped whoopie pies, you can lightly trace a 1 ½-2 inch heart-shaped cookie cutter onto your parchment paper. This helps maintain uniform size and shape. Remember to flip the parchment paper over so the pencil marks don’t transfer to your cakes. If you prefer, you can also freehand the shapes – they’ll taste just as good!
Piping chocolate cake batter onto parchment paper in heart shapes for whoopie pies
*Tip: Notice the generous space between the two halves of the heart as you pipe. This is crucial because the whoopie pie cakes will expand and nearly double in size as they bake. If they are piped too closely, they might bake together and lose their distinct heart shape. Give them room to grow!
  • Transfer the cake batter to a pastry bag fitted with a ½-inch round tip, or simply use a sturdy ziplock bag with one corner snipped off to create a ½-inch opening.
  • Carefully pipe the heart shapes (or circles) onto the prepared parchment paper, ensuring you leave ample space – about 1 to 2 inches – between each one. This allows them to rise evenly and prevents them from merging during baking.
  • Baked heart-shaped chocolate whoopie pie halves on a cooling rack

  • Bake in the preheated oven for approximately 7-8 minutes, or until the edges are set and the centers spring back lightly when touched. Avoid overbaking to keep them moist.
  • Once baked, remove the cookie sheet from the oven and let the whoopie pie halves cool on the sheet for 2 minutes before carefully transferring them to a wire cooling rack to cool completely. They must be entirely cool before filling.

Crafting the Dreamy Strawberry Cream Cheese Filling

The star of these whoopie pies is undoubtedly the vibrant, creamy strawberry filling. This buttercream combines the richness of butter and cream cheese with the sweet, fruity burst of strawberry jam, creating a filling that’s both luscious and irresistible. Here’s what you’ll need for this delightful center:

Ingredients for Strawberry Cream Cheese Filling including unsalted butter, cream cheese, vanilla extract, strawberry jam, and powdered sugar

  • Unsalted butter, softened
  • Cream cheese, softened (full-fat for best texture)
  • Vanilla extract
  • Strawberry jam (good quality for intense flavor)
  • Powdered sugar (confectioners’ sugar)

How to Make the Creamy Strawberry Filling

Preparing this luscious filling is incredibly simple and yields a wonderfully flavorful result:

Prepared Strawberry Cream Cheese Filling in a bowl, ready to be piped

  • In a large bowl, using an electric mixer, cream together the softened butter and cream cheese until the mixture is light, fluffy, and completely smooth. This step is crucial for a smooth filling, so ensure there are no lumps of butter or cream cheese.
  • Add the vanilla extract and strawberry jam to the creamed mixture. Mix until everything is thoroughly incorporated and the color is a beautiful, uniform pink.
  • Gradually begin beating in the powdered sugar, one cup at a time, until the filling reaches a thick, creamy, and spreadable consistency. If the filling is too thick, you can add a tiny splash of milk or cream; if it’s too thin, add a bit more powdered sugar.

Assembling Your Perfect Chocolate Strawberry Whoopie Pies

Now for the fun part – bringing your whoopie pies to life! This is where the magic happens, transforming simple cake halves and a dreamy filling into a cohesive, delectable treat:

Piping strawberry cream cheese filling onto one half of a chocolate whoopie pie

  • Once your chocolate cake halves are completely cooled, take one half and either spread or pipe a generous amount of the strawberry cream filling onto its flat side. You can use a knife, an offset spatula, or a pastry bag for a neat, swirled effect.
  • Placing another chocolate whoopie pie half on top of the filling to assemble

  • Gently place another cooled chocolate cake half on top of the filling, pressing down just enough to create a sandwich. Avoid pressing too hard, which could squeeze out too much filling.
  • Repeat this process until all your whoopie pies are assembled. This recipe should yield approximately 2 dozen delectable whoopie pies, depending on the size you pipe them.
  • Once assembled, it’s best to refrigerate the whoopie pies. The cream cheese filling benefits from chilling, firming up slightly and making them even more enjoyable.

Finished Chocolate Strawberry Whoopie Pies stacked on a cake stand

Pro Tips for Whoopie Pie Perfection: Pans and Freezing

For those who love convenience and perfectly uniform whoopie pies, a dedicated whoopie pie pan can be a game-changer. These specialty pans have indentations that guide your batter into perfectly shaped circles (or even hearts!), eliminating the need for tracing or precise piping skills. It’s a fantastic tool to have if you plan on making whoopie pies often, ensuring each one is consistently sized and baked. You can find standard whoopie pie pans and even charming heart-shaped ones online.

Heart-shaped Chocolate Strawberry Whoopie Pies dusted with powdered sugar

A whoopie pie pan showing multiple round cavities for baking

Freezing Whoopie Pies for Later Enjoyment

These whoopie pies are so delicious, you might want to make a double batch and save some for later! Whoopie pies freeze beautifully, allowing you to enjoy a homemade treat whenever the mood strikes. To freeze them, I recommend wrapping each individual whoopie pie tightly in plastic wrap, then placing them in an airtight freezer-safe container or a heavy-duty freezer bag. They can be stored in the freezer for up to 3 months. When you’re ready to enjoy one, simply transfer it to the refrigerator to defrost for a few hours. This makes them perfect for meal prepping your desserts or having a stash for unexpected guests.

What Exactly is a Whoopie Pie? Unraveling the Delicious Mystery!

The whoopie pie is a delightful dessert with a rather curious name, often leading to questions about its true identity: Is it a pie? A cookie? Or a cake? The truth is, whoopie pies aren’t pies at all. They are essentially two soft, cake-like cookies (often referred to as “rounds” or “gobs” in some regions) sandwiched together with a creamy, fluffy filling. Think of it as a decadent, oversized, and much softer version of an Oreo, or perhaps an “inside-out” cupcake where the frosting is generously layered between two cakey discs.

Historically, whoopie pies are believed to have originated in the Pennsylvania Amish country, with strong ties also to New England and Maine. Legends suggest that when Amish women would bake these treats from leftover cake batter, their husbands or children would exclaim “Whoopie!” upon finding them in their lunch pails. While people in Nebraska, like myself, might not have grown up with them (the closest I encountered was an Oatmeal Pie, but that’s a tale for another time), their deliciousness couldn’t be contained. Over time, whoopie pies began their tasty migration across the country, much to the delight of dessert lovers everywhere.

Chocolate Covered Strawberry Baked Donuts on a pink plate

The Cake Mix Advantage for Fluffy Whoopie Pies

While traditional whoopie pie recipes often call for ingredients from scratch, my version leverages the convenience and consistent results of a good quality cake mix. Many bakers find that scratch whoopie pies can sometimes turn out a bit flat or dense. Using a cake mix, however, virtually guarantees that light, fluffy, and perfectly soft cake-cookie texture that makes whoopie pies so irresistible. When I decided to try my hand at these wonderful treats, I chose to skip the potential fuss and embrace the cake mix, ensuring a consistently delicious and easy outcome every time. It’s a smart shortcut that doesn’t compromise on flavor or the signature pillowy soft texture.

Explore More Chocolate Strawberry Delights & Sweet Inspirations

The incredible flavor pairing of chocolate and strawberry is simply unmatched, making it ideal for Valentine’s Day or any occasion that calls for a touch of sweet decadence. If you adore this combination, you’ll be thrilled to discover other wonderful recipes to try!

For another delightful chocolate strawberry treat, don’t miss these Chocolate Covered Strawberry Baked Donuts. Imagine light, tender strawberry donuts, baked to perfection, then generously glazed with a rich chocolate frosting. They are truly delicious and a perfect alternative to fried donuts!

Looking for even more ideas? Explore a bounty of sweet inspirations perfect for Valentine’s Day and beyond:

Discover All My Valentine Recipes & Ideas

Other Whoopie Pie Varieties to Explore:

If you’ve fallen in love with whoopie pies and want to try more flavors, here are some fantastic recipes from my kitchen and those of my talented baking friends:

  • Classic Maine Whoopie Pies
  • Chocolate Salted Caramel Whoopie Pies
  • Apple Butter Whoopie Pies
  • Chocolate Fluffernutter Whoopie Pies
  • Funfetti Whoopie Pies

Close-up of a delectable Chocolate Strawberry Whoopie Pie, showing the fluffy cake and creamy filling

Wishing you a Valentine’s Day filled with warmth, affection, and plenty of these adorable “sweetie pies” — Heart Shaped Chocolate Strawberry Whoopie Pies! Happy baking!

Michaela Kenkel's signature

LIKE THIS RECIPE?
Don’t forget to give it a ⭐️⭐️⭐️⭐️⭐️ star rating and
leave a comment below the recipe!

overhead of Chocolate Strawberry Whoopie Pies shaped like hearts in a green bowl
4.50 from 6 votes

Print Recipe

Chocolate Strawberry Whoopie Pies

Chocolate Strawberry Whoopie Pies simply made with a Devil’s food cake mix, piped in the shape of a heart or a circle, frosted with strawberry buttercream made with strawberry jam. For Valentine’s Day or any other day you just need a little chocolate strawberry whoopie pie love in your life!
Prep Time20
Cook Time8
Total Time28
Cuisine: American
Keyword: Chocolate Strawberry Whoopie Pies, heart shaped, strawberry cream filling, Valentines Day, what is a Whoopie Pie? How to make Whoopie Pies, whoopie pie recipe
Servings: 2 dozen
Calories: 237kcal
Author: Michaela Kenkel

Equipment

  • Kitchenaid Stand Mixer
  • KitchenAid Hand Mixer
  • Fox Run Mini Heart Muffin Pan
  • Wilton 12-Cavity Whoopie Pie Baking Pan
  • Reynolds Kitchens Non-Stick Parchment Paper
  • 13×18 Half Sheet Pan

Ingredients

  • For the pies:
  • 1 box Devils Food cake mix
  • 3 large eggs room temperature
  • ½ cup vegetable oil
  • 2 teaspoons vanilla extract
  • For the filling:
  • 4 Tablespoons unsalted butter softened
  • 6 ounce cream cheese softened
  • ½ teaspoon vanilla extract
  • ¼ cup strawberry jam
  • 3 cups powdered sugar

Instructions

  • To prepare the Whoopie Pies: Preheat the oven to 350 degrees F (175 C). Line cookie sheets with parchment paper.
  • In a large bowl, with a mixer combine cake mix, eggs, oil and extract until incorporated. Then beat on medium speed for 2 minutes.
  • Trace a heart-shaped cookie cutter on your parchment paper to get the hearts all the same size (or you can freehand it, up to you). Hearts should be about 1 ½-2” in size. Flip the parchment paper over so pencil tracing is facing down, preventing transfer to cakes.
  • Fill a pastry bag or a ziplock bag with the cake batter and clip off the corner (or add a pastry tip). The opening should be about 1/2” in size.
  • Pipe the hearts onto the parchment paper leaving a couple of inches of space in between them for them to rise/spread out when they bake. **Make sure to leave a pretty good gap in the middle so the hearts stay heart-shaped when they bake.**
  • Bake until edges are set, about 7-8 minutes, then cool on the cookie sheet for 2 minutes before removing them to a cooling rack to cool completely.
  • To Prepare the Strawberry Cream Filling: With a mixer, cream together softened butter and cream cheese until fluffy. Add in vanilla and jam and mix until incorporated. Gradually beat in the powdered sugar until creamy and smooth.
  • Spread or pipe the filling onto one-half of the cookies, then top with another half to create a sandwich.
  • Refrigerate the assembled whoopie pies. They can be frozen for up to 3 months in an airtight container. Defrost in the refrigerator before enjoying.

Nutrition

Serving: 1 | Calories: 237kcal | Carbohydrates: 34g | Protein: 2g | Fat: 10g | Saturated Fat: 4g | Polyunsaturated Fat: 6g | Cholesterol: 36mg | Sodium: 192mg | Sugar: 25g