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Rustic Chocolate Whoopie Pies with Caramel Baileys Cream Cheese Filling

Too many times have I come across a recipe that claims to be “rustic.” Like a rustic cheesecake, rustic flatbread, or rustic pasta. I mean, what makes these recipes rustic? The styling of the photo? The ingredients? The method of assembly? I never understood until now what makes a recipe “rustic.”

Rustic Chocolate Whoopie Pies

You see, I kind-of messed-up these whoopie pies. The batter was too thick resulting in a chunkier, lumpy cookie vs. a flat smooth cookie. Don’t get me wrong, they were absolutely delicious, just a little more rustic than I would have liked (you see what I did there?). So, at least for me, when I mess up a recipe or it looks a little less perfect, I’m going to call it “rustic.” Like I meant to do. Totally on purpose. But that will be our little secret!

Rustic Chocolate Whoopie Pies

I also had a pretty heated internal debate as I waited for the cookies to cool. Did I want a traditional peanut butter filling, or did I want to go for something more fun like a caramel Baileys cream cheese filling? I love a good classic combo, but there is something about Baileys that takes it all up a notch… To be honest I was dead set on the peanut butter until I realized I didn’t have a single jar of peanut butter in my pantry! Caramel Baileys it was!

Rustic Chocolate Whoopie Pies

Rustic Chocolate Whoopie Pies with Caramel Baileys Cream Cheese Filling

The thicker cookie on these chocolate whoopie pies make these traditional sweet treats a little more rustic. The cream cheese filling is so versatile and can be flavoured any way you like – peanut butter, Baileys, or even more chocolate!

Chocolate Cookies
1 2/3 cups all-purpose flour
2/3 cup unsweetened cocoa powder
1 1/2 teaspoons baking soda
1/2 teaspoon salt
8 tablespoons butter, room temperature
1 cup packed brown sugar
1 egg
1 teaspoon vanilla
1 cup milk (I used almond milk)

1. Preheat your oven to 375 and line a baking sheet with parchment paper.
2. In a medium bowl, sift together, flour, cocoa, baking soda, and salt.
3. In another larger bowl, beat butter and sugar with a mixer just combined. Increase speed to medium and beat for 3 minutes.
4. Add egg and vanilla and beat for 2 minutes.
5. Add half of the flour mixture and milk and beat on low until incorporated. Repeat with remaining flour and milk until batter is combined.
6. Using a spoon, drop batter onto a parchment lined baking sheet, about 2 inches apart.
7. Bake for 10 minutes or until pies spring back when gently pressed.
8. Remove and cool for 5 minutes before transferring them to a wire rack to cool completely.
9. Once cool, you can either pipe or spread room-temperature cream cheese filling onto flat side of cookie. Top with another cookie and press together gently. Enjoy right away!

Caramel Bailey’s Cream Cheese Filling
8 oz cream cheese, at room temperature
1/4 cup butter, at room temperature
3-4 tablespoons Caramel Baileys
3 cups powdered sugar

1. In a bowl, blend together the cream cheese, butter, and Baileys on medium speed until smooth and combined.
2. Gradually add powdered sugar on medium-low speed until it has all been added.
3. Increase mixer speed to medium-high and beat until frosting is smooth.
4. Use immediately.

Other than the “rustic” look of these whoopie pies, there was absolutely nothing wrong with them! And you can bet your bottom dollar that the next time I have peanut butter in the house a fresh batch of Chocolate Peanut Butter Whoopie Pies will be made!

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  1. These look amazing! Good call on the Bailey's! Barefoot Contessa uses rustic all the time…she says things don't have to perfect! People just want to eat them!

  2. I'm happy with the Bailey's flavour – it added just the right amount finesse! And yes, I didn't care how they looked, I just wanted to eat every single one of them!