I had a vague notion of what a whoopie pie was when I started seeing more recipes pop up.  Like candy bars and soda, whoopie pies seem distinctly American to me.  I didn’t grow up hearing about or seeing any whoopie pies.  They weren’t at specialty bakeries or brought out at birthday parties.  From what I could tell, they were essentially a homemade sandwich cookie. I’ll always choose Chips Ahoy over Oreo, so the attraction was minimal.  But when I saw the enticing variations that cropped up via Lucy Waverman’s recipe in The Globe and Mail and Jeremy’s over at The Kitchen Front, I felt these were waters beyond chocolate and vanilla that I wanted to wade into.  After deciding to make a sweet treat for a Halloween gathering, I set my sights on Martha Stewart’s chocolate-pumpkin version as I had some leftover canned pumpkin at the ready.

All was going fine until I was ready to ice my pies.  I thought nothing of the puff my cookies held when coming out of the oven.  They would deflate upon cooling and I would have perfect little pies.  Not so.  No deflation.  No cooperative pies that would lay flat and look pretty. Oh, the science of baking.  There was some slight mismeasurement in my chemistry (baking) project, and my cookies rose too much.  A friend at the party was very excited to try one of my “pods.”  Alien-like or not, they were still pretty tasty.  And… when I saw that these tasty looking whoopie pies also came out as pods, I didn’t feel so bad.

Two bites in...

One bite in and you know you’re not dealing with just a sandwich cookie.  The texture of the cookies is very cake-like, and Martha’s batter did not disappoint with its rich, chocolate flavour.  The tang of the cream cheese in the icing was an appropriate complement to the rich cookies, and the pumpkin made you wonder why the chocolate-pumpkin combination has not been exploited further.  Black bottom pumpkin pie anyone?  My overarching thought on the pie, however, was that it was not a homemade sandwich cookie.  It is a reconfigured cupcake — a homemade cupcake sandwich.  A traditional cookie batter would likely just crumble with each bite.  Cake, not so much.  Does this mean we’ll soon see a whoopie pie shop on every corner?!

And yes, we are very happy to be celebrating our second birthday as Cream & Sugar.  Thank you very much for reading.

Chocolate-Pumpkin Whoopie Pies
adapted from Martha Stewart

1 3/4 cups all purpose flour
3/4 cup unsweetened cocoa powder
1 1/2 teaspoons baking soda
1/2 teaspoon coarse salt
1/4 cup + 1 tablespoon unsalted butter, softened
1/2 cup granulated sugar
1/2 cup packed dark brown sugar
1 large egg
1 cup whole milk
1 teaspoon pure vanilla extract

4 ounces cream cheese, at room temperature
1/2 cup unsalted butter, at room temperature
1/2 cup icing sugar
1/4 cup canned pumpkin
1/4 teaspoon of cinnamon
Pinch of nutmeg

Preheat oven to 375 degrees. Sift together flour, cocoa powder, baking soda, and salt into a medium bowl; set aside.
Beat butter and sugars with a handheld mixer in a large bowl. Mix on high speed until smooth, about 3 minutes. Add egg; mix until pale and fluffy, about 2 minutes. Mix in half the flour mixture, then the milk and vanilla. Mix in remaining flour mixture.
Drop about 1 tablespoon amounts of dough onto baking sheets lined with parchment paper, spacing 2 inches apart. Bake until cookies spring back when lightly touched, 12 to 14 minutes. Transfer baking sheets to wire racks and let cool 10 minutes. Remove cookies from baking sheets and transfer to wire racks using a spatula; let cool completely.
Whip together cream cheese, butter and icing sugar on medium speed until smooth, about 3 minutes. Add pumpkin, cinnamon, and nutmeg; whip until smooth, scraping down the bowl as necessary. Spoon about 2 teaspoons filling on the flat sides of half the cookies. Sandwich with remaining cookies.  Makes about 15-18.