Whoopie Pies are a fun and delicious alternative to cupcakes and a little bit more special than a cookie. In all honesty, whoopie is a fun word say! It totally reminds of the game show part of Mallrats! Anyway, a whoopie pie is a cake-like cookie with a frosting filling. The most traditional whoopie pie is a chocolate cake with a marshmallow cream filling. I like the cookbook Whoopie Pies because you are provided with a bunch of whoopie recipes and then a bunch of filling recipes, there are suggestions, but it’s fun to mix and match.
I made these for a dinner party at my friend Kristin’s house. She is a pretty sophisicated lady who has spent a lot of time in Italy. My first thought was to make cupcakes, but I wanted to try something different. The flavors of tiramisu came through really well in the filling and the whoopie part was moist and delicious. I went with chocolate chips instead of a plain vanilla whoopie because I always believe tiramisu can use a little bit more chocolate. These whoopies received rave reviews from both the dinner party guests and my co-workers who were able to sample leftovers at work on Saturday!
Using a small cookie scoop is the ideal way to portion out the whoopies. It helps them to stay nice and round and evenly sized. Usually I use a pipping bag for the filling, but I just wasn’t feeling it. I wanted to dip the edges cocoa powder to look like the top of a traditional tiramisu, but then I wanted more chocolate chips, so I did a little of both!
Tiramisu Whoopie Pies
Adapted from Whoopie Pies by Sarah Billingsley & Amy Treadwell, page 50 & 98
Yield – 20 whoopie pies
2 1/4 cups flour
1 1/2 teaspoons baking powder
1/2 teaspoon salt
4 tablespoons unsalted butter, room temperature
4 tablespoons shortening
1/2 cup packed light brown sugar
1/2 cup buttermilk (just use a scant half a cup with a teaspoon of lemon juice)
2 tablespoons milk
1 teaspoon baking soda
1 teaspoon white vinegar
1/2 teaspoon vanilla extract
1 cup mini chocolate chips
- Line 3 baking sheets with parchment paper and preheat the oven to 350 F.
- Sift together the flour, powder, and salt onto parchment paper.
- Beat together the butter, shortening, and sugars in the bowl of a stand mixer with a paddle attachment on medium speed until light and fluffy. Add in the eggs and buttermilk and beat together.
- Mix the milk, soda, and vinegar together and then add to the batter. Add in the vanilla and beat for 2 minutes on medium so that everything is well combined.
- Use a rubber spatula to mix in the mini chocolate chips.
- Use a 2 tablespoon cookie scoop to portion the batter on the baking sheets. I was able to fit 10-12 whoppies per baking sheet. Leave space for the whoopies to spread slightly. (please ignore the creepy hand shadows)
- Bake for 10 minutes or until the edges just begin to brown.
- Transfer to a cooling rack.
Cream filling & assembly
4 cups powdered sugar
8 ounces mascarpone cheese
4 tablespoons butter, room temperature
1 tablespoon strong coffee
1/2 teaspoon vanilla
1 teaspoon rum
Cocoa powder and chocolate chips for dipping
- Beat the butter and mascorpone cheese together in a stand mixer with a paddle attachment. Add in the powdered sugar 1 cup at a time and beat on low speed until combined and then turn the mixer on high.
- Slowly add the vanilla, coffee, and rum, mix until light and fluffy.
- Match the cooled whoopies with a friend that is most similar in size.
- Spread about 1 1/2-2 tablespoons of filling on one half. Push the filling to the edge.
- Put the whoopies together and then dip & roll in mini chocolate chips of cocoa powder.