Pumpkin Whoopie Pies

pumpkin whoopie piesI’ve never been a huge Pumpkin Pie fan. I know, call it blasphemy, especially on the holiday that wouldn’t be complete without it. Unless, that is, you make a pumpkin roll – but that just seems way too old-fashioned or Paula Deen for my tastes.

Enter: The Pumpkin Whoopie Pie. The perfect mixture of cake and frosting, sandwiched together in the most decadent individual serving with all the flavors of fall. You’re sure to satisfy the traditionalists but intrigue even the most picky of eaters.

This is adapted from Matt Lewis’s recipe via marthastewart.com. He serves these bad-boys seasonally at his super awesome Red Hook bakery, Baked, of which I’m a HUGE fan. Some minor changes have been made but the bones of the recipe are all his. So without further adieu, here you have it:


For The Cream-Cheese Filling:

  • 3 cups confectioners’ sugar
  • 1/2 cup butter, softened
  • 8 ounces organic cream cheese, softened
  • 1 teaspoon pure vanilla extract

For The Pumpkin Whoopie Cookies:

  • 3 cups organic AP Flour
  • 1 teaspoon salt
  • 1 teaspoon baking powder
  • 1 teaspoon baking soda
  • 2 tablespoons ground cinnamon
  • 1 tablespoon ground ginger
  • 1 tablespoon ground cloves
  • 2 cups firmly packed dark-brown sugar
  • 1 cup Walnut Oil
  • 3 cups pumpkin puree, chilled
  • 2 large eggs
  • 1 teaspoon pure vanilla extract


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

In a large bowl, whisk together flour, salt, baking powder, baking soda, cinnamon, ginger, and cloves; set aside. In another 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.

Drop heaping tablespoons of dough onto prepared baking sheets in even circular mounds, about 1 inch apart. 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.

For the frosting, sift confectioner’s sugar into a medium bowl and 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.

To assemble the whoopie pies: Line a baking sheet with parchment paper and set aside. Transfer filling to a ziplock bag and snip the end. When cookies have cooled completely, squeeze 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.

The Whoopie Pies can be kept in the fridge for a couple days, so this it the perfect make-ahead dessert. Bake these on Wednesday, and they’ll be perfect on Thursday. And I promise you, no one will miss the pumpkin pie!