Pumpkin Whoopie Pie Cookies

If you’re looking for cookies that make you weep with happiness, this is your lucky day. These whoopie pie cookies with a creamy to-die-for pumpkin cream cheese filling will leave you a blubbering wreck. Side note: if you want to avoid people giggling every time you say “whoopie” you can call them sandwich cookies, everything an Oreo wishes it could be in its wildest dreams.

Here’s what you’ll need:

For the cookies:

1 stick unsalted butter, at room temperature
1 1/4 cups granulated sugar
1 large egg
1 cup buttermilk, at room temperature
1 teaspoon pure vanilla extract
1 3/4 cups all-purpose flour
3/4 cup unsweetened cocoa powder
1 1/2 teaspoons baking soda
1/2 teaspoon baking powder
Pinch of kosher salt

For the filling:

5 ounces cream cheese
4 tablespoons unsalted butter, at room temperature
2/3 cup confectioners’ sugar
1/3 cup canned pure pumpkin
1/2 teaspoon ground cinnamon
Pinch of salt

First, make the cookies. Thoroughly grease a cookie sheet (or line it with parchment paper). Chocolate cookies are insanely good, but they’re also the easiest to burn. Preheat the oven to 400 degrees. In a mixing bowl, beat together the butter and granulated sugar until fluffy. Then add the egg, buttermilk, and vanilla and beat some more. In a separate bowl, sift the flour, cocoa powder, baking soda, baking powder, and salt. Slowly add the dry mixture to the creamed ingredients, mixing until combined.

Drop cookie dough on baking sheet in balls a little larger than a quarter. Bake until the edges are set but the cookies are still soft in the middle, about 5 or 6 minutes. I watch them carefully to make sure they don’t burn. Remove from oven and let cookies cool 2 minutes on the baking sheet, then transfer to a plate to let them finish cooling.

To make the delectable filling: beat the cream cheese and butter in a small bowl until smooth. Slowly add in the confectioners’ sugar until smooth. Add the pumpkin, cinnamon, and salt and beat some more until smooth.

To assemble the whoopie pies, spread a heaping tablespoon of pumpkin mixture on the flat side of a cookie and top with another cookie. Repeat with all the cookies. Then attack them like a cookie monster.

*Pro-tip: we buy actual cinnamon sticks and grind our own cinnamon. I promise you, freshly ground cinnamon makes a pretty big difference in quality.