I’ve never really embraced the warm, pumpkin-y, cinnamon-y flavors of Fall (they make me feel bitter that summer’s over), but I’m coming around in a major way. This month, I’ve discovered the joys of cooking and baking with pumpkin. While kicking myself (really, really hard) for missing out on it for so long, I’ve been making up for lost time, making about half a dozen pumpkin recipes in just the last couple of weeks. If I had to pick a favorite, it would be Pumpkin Whoopie Pies with Cream Cheese Frosting!

(Image by me! Originally posted here)

A whoopie pie is a cake-like sandwich cookie with a creamy filling (in this case, cream cheese frosting). I had never tried one before, so I don’t have much to compare it to, but these were most definitely worthy of the name whoopie! They were also incredibly easy to make, and made me extra happy because I got to use Baked, one of my favorite cookbooks. I highly recommend Baked if you’re interested in creative twists on classic baked goods (i.e. Root Beer Bundt Cake and a cinnamon-y Red (Hot) Velvet Cake).

If you make these, I’d love to hear what you think!

Pumpkin Whoopie Pies with Cream Cheese Filling
Adapted from Baked: New Frontiers in Baking
Printable Recipe
Makes 18 Whoopie pies

For the Pumpkin Whoopie Cookies:
3 cups all-purpose flour
1 teaspoon salt
1 teaspoon baking powder
teaspoon baking soda
4 teaspoons pumpkin pie spice
2 cups firmly packed dark-brown sugar
1 cup vegetable oil
3 cups pumpkin puree, chilled
2 large eggs
1 teaspoon pure vanilla extract

For the Cream Cheese Filling:
3 cups confectioners’ sugar
1/2 cup (1 stick) unsalted butter, softened
8 ounces cream cheese, softened
1 teaspoon pure vanilla extract

1. Preheat oven to 350 degrees. Line two baking sheets with parchment paper or a nonstick baking mat; set aside.

2. In a medium bowl, whisk together flour, salt, baking powder, baking soda, and pumpkin pie spice; set aside. In a large bowl, whisk together brown sugar and oil until well combined. Add pumpkin puree and whisk until combined. Add eggs and vanilla and whisk until well combined. Sprinkle flour mixture over pumpkin mixture and whisk until fully incorporated.

3. Using a small ice cream scoop with a release mechanism, drop heaping tablespoons of dough onto prepared baking sheets, about 1 inch apart. Transfer to oven and bake until cookies are just starting to crack on top and a toothpick inserted into the center of each cookie comes out clean, about 15 minutes. Let cool completely on pan.

4. Make the filling: Sift confectioner’ sugar into a medium bowl; set aside. In the bowl of an electric mixer fitted with the paddle attachment, beat butter until smooth. Add cream cheese and beat until well combined. Add confectioners’ sugar and vanilla, beat just until smooth. (Filling can be made up to a day in advance. Cover and refrigerate; let stand at room temperature to soften before using.)

5. Assemble the whoopie pies: Line a baking sheet with parchment paper and set aside. Using a small ice cream scoop or tablespoon, place a large dollop of filling on the flat side of half of the cookies. Sandwich with remaining cookies, pressing down slightly so that the filling spreads to the edge of the cookies. Transfer to prepared baking sheet and cover with plastic wrap. Refrigerate at least 30 minutes before serving and up to 3 days.