Chocolate Chip Red Velvet Whoopie Pies — Sweet Southern Celebration for MawMaw Shirley

Graduation week approaching. Mama is planning the after-party with military precision. Daddy is selecting the grill menu. MawMaw Shirley called to say she is coming — "I did not miss the high school graduation and I will not miss this one." She will be eighty-one. She will wear the hat. She will say "Doctor Robinson." And she will be right.

I practiced the gumbo for twenty people — the graduation feast. Three pots. MawMaw Shirley's recipe tripled. The math of feeding a family is the math of love multiplied.

While the gumbo is the heart of MawMaw Shirley’s legacy and the centerpiece of the graduation feast, every great Southern spread needs something sweet to close it out — something that looks as celebratory as it tastes. These Chocolate Chip Red Velvet Whoopie Pies are exactly that: bold, red, and joyful, worthy of the woman who will walk in wearing her hat and say “Doctor Robinson” like she always knew it was coming. I made a triple batch, same as the gumbo — because when eighty-one-year-old MawMaw Shirley travels to be there, you do not run out of dessert.

Chocolate Chip Red Velvet Whoopie Pies

Prep Time: 25 min | Cook Time: 12 min | Total Time: 45 min | Servings: 12 whoopie pies

Ingredients

• 2 cups all-purpose flour
• 2 tablespoons unsweetened cocoa powder
• 1 teaspoon baking soda
• 1/2 teaspoon salt
• 1/2 cup unsalted butter, softened
• 1 cup granulated sugar
• 2 large eggs, room temperature
• 1 teaspoon pure vanilla extract
• 1 tablespoon red food coloring
• 1/2 cup buttermilk
• 1 teaspoon white vinegar
• 1 cup semi-sweet chocolate chips
• Cream Cheese Filling:
• 8 oz cream cheese, softened
• 1/4 cup unsalted butter, softened
• 2 cups powdered sugar, sifted
• 1 teaspoon pure vanilla extract

Instructions

1. Preheat. Heat oven to 350°F. Line two large baking sheets with parchment paper.
2. Mix dry ingredients. In a medium bowl, whisk together flour, cocoa powder, baking soda, and salt. Set aside.
3. Cream butter and sugar. In a large bowl, beat softened butter and granulated sugar with an electric mixer on medium speed until light and fluffy, about 3 minutes.
4. Add eggs and color. Beat in eggs one at a time, then mix in vanilla extract and red food coloring until fully incorporated and the batter is evenly crimson.
5. Combine wet and dry. In a small bowl, stir together buttermilk and white vinegar. With the mixer on low, alternate adding the flour mixture and buttermilk mixture to the butter mixture, beginning and ending with flour, mixing just until combined after each addition.
6. Fold in chips. Using a rubber spatula, gently fold in the chocolate chips.
7. Portion and bake. Drop rounded tablespoons of batter onto prepared baking sheets, spacing about 2 inches apart. Bake 10 to 12 minutes, until the tops spring back lightly when touched. Do not overbake. Cool on the pan for 5 minutes, then transfer to a wire rack to cool completely.
8. Make the filling. Beat cream cheese and butter together until smooth and fluffy. Add powdered sugar one cup at a time, beating well, then mix in vanilla. The filling should be thick and spreadable.
9. Assemble. Match cake rounds into pairs by size. Spread or pipe a generous layer of cream cheese filling onto the flat side of one round, then press its partner gently on top. Repeat with remaining rounds.
10. Chill before serving. Refrigerate assembled whoopie pies for at least 15 minutes to set the filling. Store covered in the refrigerator for up to 3 days.

Nutrition (per serving)

Calories: 385 | Protein: 4g | Fat: 19g | Carbs: 51g | Fiber: 1g | Sodium: 215mg