Chocolate Chip Whoopie Pies

Having baked so often over the past few years, I think I’ve finally figured out what I can count on Shane to eat, and what needs to be shared with family/friends unless I want it to sit on the counter untouched for a week.  Breakfast items – muffins, scones, quick breads – fall completely in my domain; Shane shows little to no interest.  The situation is similar with pies and tarts.  Cupcakes are always popular, unless they include fruit.  Same with homemade ice cream.  One thing that’s really surprised me is how little love cookies get around here.  Even a batch of double chocolate cookies (among Shane’s favorites) might be slow to disappear.  The most surefire way to make them more appealing is to add a filling – whoopie pies are definitely the new “it” thing around our house.  Shane is obsessed with them lately, and I love making them, so it’s a double win.

I’d recently baked a batch of whoopie pies (post coming next week) and the same day we polished them off I heard Shane say “I wish we had more whoopie pies.”  I think he was hoping for the same flavor, but instead I grabbed my whoopie pie book from the shelf, letting him thumb through and choose the next variation.  These chocolate chip whoopie pies were the winner; I decided to pair them with a chocolate buttercream for the filling.  We really enjoyed the combination, though I think you could go any number of different ways with these and still be happy.  The cookies themselves are sturdy, but still tender.  I always use a cookie scoop to portion the batter when I make whoopie pies so the cookies will be easier to pair up by size.  These baked a little less uniformly than I’d have liked, so the matching was a bit challenging, but I’m a huge perfectionist about things like that so I’m not sure anyone else would even noticed.

Oh, and if for some reason you’re not into chocolate buttercream, make the cookies and do this with them:

That’s a big scoop of vanilla ice cream, and honestly, became my favorite way to enjoy the cookies.

Chocolate Chip Whoopie Pies with Chocolate Buttercream
from Whoopie Pies by Sarah Billingsley and Amy Treadwell

Cookies
2 1/4 cups all-purpose flour
1 1/2 teaspoons baking powder
1/2 teaspoon salt
4 tablespoons unsalted butter, at room temperature
4 tablespoons vegetable shortening
1/2 cup granulated sugar
1/2 cup packed light brown sugar
2 large eggs, at room temperature
1/2 cup buttermilk, at room temperature
2 tablespoons milk
1 teaspoon baking soda
1 teaspoon white vinegar
1/2 teaspoon vanilla extract
1 cup mini chocolate chips

Preheat oven to 375 F. Line two baking sheets with parchment paper.

Whisk the flour, baking powder and salt together in a medium bowl. In the bowl of a stand mixer fitted with the paddle attachment, cream the butter, shortening and both sugars on medium speed until light and fluffy, about 3-4 minutes. Mix in the eggs and buttermilk, beating until combined (the mixture may look curdled, don’t worry it’ll come together).

In a small measuring cup, stir together the milk, baking soda and vinegar. Add to the batter along with the dry ingredients (all at once) and beat on low speed just until combined. Mix in the vanilla then beat on medium speed for about a minute, until all ingredients are incorporated and the batter is light. Stir in the chocolate chips.

Use a small cookie scoop (mine is a #50) to drop the batter onto the prepared baking sheets, 12 cookies to a sheet. Bake, one sheet at a time, for 9-10 minutes, or until the edges of the cookies begin to brown and they spring back when lightly pressed in the center. Transfer the baking sheet to a wire rack and let the cookies cool for 5 minutes before transferring them to the wire rack to cool completely. Repeat with remaining slice.

Buttercream
1 1/3 cups confectioners’ sugar
1/2 cup unsweetened cocoa powder
4 tablespoons unsalted butter, at room temperature
3 tablespoons heavy cream
1 teaspoon vanilla extract
1/2 teaspoon salt

In the bowl of a stand mixer fitted with the paddle attachment, sift together the confectioners’ sugar and cocoa powder. Add the butter and beat on low until the mixture is crumbly. Add the heavy cream, vanilla extract and salt and mix on high speed until the buttercream is smooth and fluffy, about 3-4 minutes.

Match the cookies in pairs by size.  Transfer the filling to a piping bag and pipe a small amount onto the flat side of one cookie of each pair.  Sandwich the cookies together, and press the filling to the edges.

Makes about 24 sandwich cookies (depending on the size of your cookie scoop)