Overview

A whoopie pie is part cookie, part pie, part cake. In other words, you’re going to want to sit down for this. This take on a whoopie pie uses cream cheese frosting sandwiched between two chocolate and yogurt infused red velvet cookies.

“We create many Whoopie Pie flavors at simplethings, but one of the most popular is our red velvet version. We add semisweet chocolate to our batter to increase the richness, not only in taste but color. These little red gems are fun to bake in teaspoon size as well. Just decrease the cooking time to 5 minutes and fill with a heaping teaspoon full of filling. We served hundreds of them at the 2011 Emmy party!” – Andy Paxson of simplethings

Ingredients

Cookies
1/3 cup (2 oz) semi-sweet chocolate chips
¾ cup (6 oz) Tillamook Unsalted Butter, melted
½ cup (4oz) Tillamook Naturally Plain Yogurt
2 eggs
1½ teaspoons apple cider vinegar
½ teaspoon vanilla
1 tablespoon red food coloring
2¼ cups (18 oz) all-purpose flour
1 cup (8 oz) granulated sugar
¼ cup (2 oz) cocoa powder
2 teaspoons  baking powder
¼ teaspoon  baking soda
½ teaspoon  salt

Filling
1 cup (8 oz) cream cheese, room temperature
3 tablespoons (1.5 oz)  Tillamook Unsalted Butter
1 teaspoon vanilla extract
2½ cups (20 oz) powdered sugar

Preparation

Make the cookies
Preheat the oven to 375°F. Place the chocolate chips in a microwave  safe bowl and cook at 50 percent power until melted, about 2 minutes. Stir until smooth. Set aside.

Whisk together the melted butter, yogurt, eggs, vinegar, vanilla, and food coloring in a bowl. In a separate bowl, stir together the flour, sugar, cocoa powder, baking powder, baking soda and salt.
Add the flour mixture to the butter mixture in three separate batches. Whisk together until completely incorporated before adding the next. Stir in the melted chocolate. Using a tablespoon measure, scoop even amounts onto a non-stick baking sheet. Bake for 8-10 minutes. Cookies will spring back slightly when touched. Cool 10 minutes before transferring to rack.

Make the filling
Beat the cream cheese with a mixer until smooth and creamy. Add the butter and beat until mixed completely. Add the vanilla and powdered sugar. Beat until smooth and no lumps appear.

Fill the cookies
Sandwich a heaping tablespoon of filling between two cookies. Repeat with all cookies.