Dirty Chai Whoopie Pies

Thick, soft, and pillowy espresso cookies sandwiched around creamy and fluffy chai spiced buttercream. These dirty chai whoopie pies are sure to be a new fall favorite!

Are we ready for fall baking? Is it still 90 degrees where you are? Yes….and yes? But seriously, is there anything better than the smell of fall spices filling your kitchen on a crisp fall Saturday? Ooooh it makes me so happy!

I’ve recently fell in love with the dirty chai latte, so naturally I had to dessert-ify it. These dirty chai whoopie pies are so thick and soft and have the creamiest buttercream filling. The cookie itself is flavored with espresso and the buttercream is packed full of homemade chai spice. These are dangerously good my friends. Ok, let’s make ’em!

How to Make Dirty Chai Whoopie Pies

Make the Espresso Cookies

Brew 1/2 C of strong coffee and set aside to cool to room temperature.Preheat the oven to 350 and line 2 cookie sheets with parchment paper.

In a medium bowl, whisk together the flour, baking powder, baking soda, cocoa powder, and salt. Set aside. In a stand mixer with the paddle attachment or in a large bowl with a hand mixer, cream the butter, oil, and sugars for 3 minutes. Add the eggs and vanilla and mix for another 2 minutes. Add the sour cream and mix until combined.

Add in half of the dry ingredients and mix until just combined with a few streaks of flour remaining. Pour in the coffee and mix to combine, starting out slow so that the coffee doesn’t splash out. Fold in the remaining dry ingredients until just combined.

Use a 1 TBSP cookie scoop to portion the dough onto the prepared cookie sheets. They will spread as they bake a little, so leave 2 inches between each cookie. Bake at 350 for 9-10 minutes, or until a toothpick comes out clean when inserted into the center of the cookies. Remove from oven and transfer to a cooling rack to cool completely. While the cookies cool, make the chai buttercream.

Make the Chai Buttercream

Add the chai spice blend to a small bowl and mix until well combined, set aside. In the bowl of a stand mixer with the paddle attachment, whip the butter on medium high speed for 10 minutes, scraping down the bowl with a rubber spatula occasionally to ensure all the butter is getting whipped. After 10 minutes, add 1/2 of the powdered sugar and mix for 3 minutes. Then, add the remaining powdered sugar and mix for another 3 minutes. Add the salt, vanilla, and 1 TBSP of the chai spice mix. Mix to combine. Add the heavy cream 2 TBSP at a time until the buttercream becomes fluffy and easy to stir by hand, but not too soft where it won’t hold its shape when piped. I used 6 TBSP of cream!

Assemble the Dirty Chai Whoopie Pies

Pair up the cookies by size and fill a piping bag with a small round tip with the chai buttercream. *Alternatively you can use a ziplock bag and snip off the top, or spread the buttercream with an offset spatula. Pipe about 2 TBSP of the buttercream on the flat side of one cookie and then press another cookie on top creating a sandwich.

*Optional- Mix 1 TBSP of the chai spice mix with 1/4 C sugar to create a chai sugar for sprinkling on top of the cookies. Serve room temperature or chilled. Cookies will keep at room temperature for 24 hours, or chilled in the fridge for up to a week.

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If you loved the recipe for these Dirty Chai Whoopie Pies, be sure to check out some of my other fall baking recipes like these Kitchen Sink Pumpkin Cookies, and these Pumpkin Cheesecake Brownies.