Tiramisu Whoopie Pies

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!

Print the Recipe!

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 sugar
1/2 cup packed light brown sugar
2 eggs
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

  1. Line 3 baking sheets with parchment paper and preheat the oven to 350 F.
  2. Sift together the flour, powder, and salt onto parchment paper.
  3. 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.
  4. 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.
  5. Use a rubber spatula to mix in the mini chocolate chips.
  6. 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)
  7. Bake for 10 minutes or until the edges just begin to brown.
  8. 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

  1. 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.
  2. Slowly add the vanilla, coffee, and rum, mix until light and fluffy.
  3. Match the cooled whoopies with a friend that is most similar in size.
  4. Spread about 1 1/2-2 tablespoons of filling on one half. Push the filling to the edge.
  5. Put the whoopies together and then dip & roll in mini chocolate chips of cocoa powder.
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Filed under Sweet Treats

2 responses to “Tiramisu Whoopie Pies

  1. Pingback: Whiskey Cupcakes | Pale Yellow

  2. Pingback: Cinnamon and Caramel Snickerdoodles | Pale Yellow

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