This recipe has been my familys favorite celebration treat for years: the perfect nostalgia of pillowy chocolate cakes sandwiched around a cloud-like marshmallow-vanilla filling. I discovered this combination while trying to recreate a childhood memory from a small bakery visit and tweaked it over several batches until the texture and balance felt just right. The cakes are tender but sturdy enough to hold a generous swirl of marshmallow buttercream, and the fillings subtle salt accent cuts through the sweetness to keep each bite interesting.

I learned early on that timing matters: letting the batter rest for 15 minutes relaxes the gluten in the cake flour and creates a finer crumb, while chilling the filling briefly helps it pipe cleanly without sinking. These pies are versatile: make them bite-sized for parties, standard size for lunches, or extra-large for showstopping desserts. Once you take a bite, youll see why this old-fashioned favorite never goes out of stylesoft, nostalgic, and endlessly satisfying.

Ingredients

• Light brown sugar (1 cup): Use packed light brown sugar for consistent moisture and a mild molasses note. I prefer the Domino or C&H brands for even granulation and flavor.
• Salted butter (1/2 cup): Room temperature butter creates an emulsion with sugar for a smooth cake texture; if your butters very salty, reduce added salt by a pinch.
• Vanilla bean paste (1 tablespoon) & coffee extract (1 teaspoon): These boost aroma and round out the chocolates flavor; vanilla bean paste gives flecks and a deeper vanilla presence than extract.
• Cake flour (2 1/4 cups): Lower protein cake flour yields a tender crumb; King Arthur or White Lily work well. Sift or whisk to remove lumps.
• Dutch-process cocoa powder (1/2 cup) & black cocoa powder (2 teaspoons): Dutch-process adds a smooth chocolate flavor; black cocoa deepens color and gives that bakery-dark look. Substitute extra Dutch-process if black cocoa is unavailable.
• Malted milk powder (2 tablespoons) & espresso/espresso powder (1/2 teaspoon): These are optional but boost chocolate complexity. Ovaltine-style malt is an easy pantry addition.
• Baking powder & baking soda: Provide lift and tenderness; measure carefully for even rise.
• Buttermilk (1 cup): Room temperature buttermilk keeps cakes tender and slightly tangy; whole-milk or cultured buttermilk are ideal.
• Filling: Unsalted butter (1 cup), butter-flavored shortening (1/2 cup), powdered sugar (4 cups), heavy cream (2 oz), marshmallow fluff (1 1/4 cups): The shortening helps stabilize the filling so it holds up at room temperature and pipes cleanly; use vegetable shortening labeled "butter flavored" for that classic taste.
• Optional garnish: Melting wafers (10 oz) and sprinkles for dipping and decoration if desired.

Instructions

Cream Butter and Sugar: In the bowl of a stand mixer, beat 1 cup packed light brown sugar with 1/2 cup room-temperature salted butter, 1 tablespoon vanilla bean paste, 1 teaspoon coffee extract, and 1/2 teaspoon salt on medium-high for 4 minutes. Scrape the bowl halfway through to ensure even creaming. This step incorporates air and creates the tender structure of the cakes. Add Egg: Add 1 large egg and beat for 1 minute until fully incorporated; scrape the sides and bottom. The egg adds structure and moisture; mix just until combined to avoid overworking. Whisk Dry Ingredients: In a separate bowl, whisk together 2 1/4 cups cake flour, 1/2 cup Dutch-process cocoa, 2 tablespoons malted milk powder, 2 teaspoons black cocoa, 1 teaspoon baking powder, 1/2 teaspoon baking soda, and 1/2 teaspoon espresso powder (optional). Ensure even distribution to prevent pockets of leavening. Alternate Dry and Wet: Add the dry ingredients to the mixer in three parts, alternating with 1 cup room-temperature buttermilk, beginning and ending with the dry. Mix on medium speed for about 1 minute until combined, then scrape and mix another 30 seconds. This technique keeps the batter smooth without overmixing. Rest and Preheat: Fold the batter gently with a spatula and let it rest for 15 minutes; preheat the oven to 350F and line two 13x18-inch baking pans with parchment. Resting relaxes gluten and helps uniform spreading. Portion and Bake: Use a #40 scoop for standard whoopie cakes (about 2 tablespoons), spacing mounds at least 3 inches apart (about 8 per sheet). Smooth peak tips with a wet finger. Bake for 911 minutes until tops spring back; larger scoops need 1012 minutes. Cool on the pan 510 minutes before transferring to a rack. Make the Filling: Cream 1 cup cold unsalted butter (cubed) with 1/2 cup butter-flavored shortening, 1 tablespoon vanilla bean paste, and 1/2 to 1 teaspoon salt for 2 minutes. Gradually add 4 cups powdered sugar with 2 ounces heavy cream, 1 cup plus 1 tablespoon at a time, scraping as you go. Fold in 1 1/4 cups marshmallow fluff until smooth and light. Taste and adjust salt or sugar for desired balance. Assemble: Scoop filling onto the bottom side of one cake and top with a matching cake, pressing gently until filling reaches the edges. For extra-stuffed pies, use two scoops of filling on half the cakes before sandwiching. Dip and Decorate (Optional): Melt 10 ounces melting wafers in 30-second bursts, stirring between intervals, and dip pies halfway. Drizzle remaining chocolate and add sprinkles while the coating is soft. Chill briefly to set.

Storage Tips

Store unfilled cake rounds in an airtight container at room temperature for up to 24 hours, or refrigerate for 23 days. For longer storage, freeze cooled rounds in a single layer on a baking sheet, then transfer to a freezer bag for up to 3 months. Thaw in the refrigerator overnight before assembling. Assembled whoopie pies with marshmallow filling keep best refrigerated and should be brought to room temperature 200 minutes before serving for the best flavor and texture. Avoid leaving dipped treats at room temperature for extended periods in warm climates.

Ingredient Substitutions

If you dont have black cocoa, use an equal amount of Dutch-process cocoa for slightly warmer color. Swap regular butter for European-style butter for a creamier mouthfeel, but reduce added salt if your butter is saltier. To make these dairy-free, use non-dairy butter substitutes and a vegan marshmallow fluff alternative, though texture will differ slightly. For a lighter filling, replace half the shortening with more butter, keeping in mind the filling may be softer at room temperature.

Serving Suggestions

Serve as individual desserts on a platter with a dusting of cocoa or a drizzle of melted chocolate. Pair with cold milk, espresso, or a scoop of vanilla ice cream for contrast. For gatherings, create a whoopie-pie bar with dipped, drizzled, and sprinkled options. Seasonal pairings include orange zest in the filling for winter holidays, or fresh raspberries and a light dusting of powdered sugar for summer picnics.

Cultural Background

Whoopie pies are a classic American confection with disputed origins between New England and Pennsylvania Dutch traditions. Often called "black moon" in some regions, they were historically a workers treat, wrapped in wax paper and packed for lunch. Over time theyve become a nostalgic staple, celebrated in festivals and reinvented by bakeries and home cooks alike. This recipe leans into classic chocolate and marshmallow flavors while using modern techniques for reliable home baking.

Seasonal Adaptations

In colder months, stir a pinch of cinnamon or orange zest into the cake batter for warmth. For spring and summer, swap the marshmallow filling for a whipped cream-and-berry layer and dip only half in a thin chocolate glaze. Holiday editions benefit from festive sprinkles, peppermint wafers, or flavored melting wafers to match themes. Adjust refrigeration and serving time for warmer months to keep shapes intact.

Meal Prep Tips

Prepare the cake rounds and freeze them flat on trays; prepare filling and store in an airtight container in the fridge. Assemble the day you plan to serve for the freshest texture. Use a piping bag to portion consistent amounts of filling and label trays to avoid mismatched sizes. For large events, bake multiple sheets in advance and store rounds unassembled to save time on the final day.

These whoopie pies are a delicious bridge between bakery nostalgia and home baking practicalitya recipe thats approachable, crowd-pleasing, and endlessly customizable. Share them warm or chilled, and enjoy the smiles they bring.