Frozen Pumpkin Whoopie Pies

I will admit. I basically saw this and thought, “I HAVE to make that. Now.” As you can see, this recipe combined two of the best baking ingredients: pumpkin, and bourbon. Life cannot get much better than this.

I am still a novice baker. I do not come from a family of bakers (at least the family members I know and love do not bake). My method of cooking–which, as you see from other posts does not include measurements or specific cooking times–does not always bode well when baking. I even have chronicled some of my harsher lessons, like realizing pie beads have a purpose.

But, these were whoopie pies. Two giant, fluffy cookies with tasty sweet blood sludge smeared between them. This could not be that difficult, right? Wrong. I screwed up the cookies. My parents and I have gone back and forth on why the cookies had issues. The best theories include “The oven sucks” (It honestly does. Very uneven. Runs cool. Timer doesn’t work. Logical explanation for the baking disaster.) and “Measuring cups know you hate them and sought vengeance” (this, clearly, is my theory).

I should say, the cookies were “screwed up” in the best way possible. You want them soft, so I pulled them out when they were soft. And then they cooled. And then I realized that they were TOO soft. There’s a simple fix, and this is where *my* version of the recipe comes into play; FREEZE THEM. It was brilliant. They became ice-cream free ice-cream sandwiches. And they still featured pumpkin and bourbon. It’s perfect.

If you’re a brilliant baker and/or if you don’t like cold desserts, go for the original. If you’re like me, and you like having “back up” options, you may want to consider the beauty of frozen whoopie pies.

N.B. By the time I realized the cookies were too soft, I was preparing to make the icing. Again, as I thought measuring cups were out to get me, I decided to make up the amounts and some of the ingredients for the icing. I hate sweets, so I purposefully used (among other things) about a third of the original amount of powdered sugar. I also happened to use significantly more bourbon. Oh well. Lah-di-da, Lah-di-da, La la…



For the cookies (makes between 10 and 12 pies, so 20-24 cookies):

  • 1 cup brown sugar
  • 1.5 cups flour
  • .5 teaspoon baking soda
  • .5 teaspoon baking powder
  • 1 egg
  • 1 can pumpkin (15 ounces)
  • .5 cups vegetable/canola oil
  • Pumpkin pie spices (nutmeg, cinnamon, ginger, cloves, allspice), to taste
  • Vanilla extract (optional)
  • Pinch of salt.

For the icing:

  • 6 ounces cream cheese, softened
  • 4-6 ounces butter, softened (but not melted)
  • Bourbon (realistically, I used the better part of an airplane bottle of Larceny)
  • Powdered sugar (probably only used half a cup tops)


  1. Preheat oven to 350*F. Line two baking sheets with parchment paper.
  2. Mix the sugar, pumpkin, egg, oil and vanilla in a bowl. Add the flour in batches until it’s fully incorporated. Toss in the baking powder/soda, and other spices to taste.
  3. Using an ice-cream scoop or a couple of large spoons, plop the batter onto the baking sheets. Try to keep the blobs as consistent as possible, and remember when they bake they’ll expand.
  4. Bake until they are “bouncy” (it’s suggested that this takes 12-15 minutes, but that probably presumes a non-diabolical oven).
  5. Set the cookies to cool. Ideally, this would be on a rack. I used silicone sheets.
  6. While the cookies cool, whip up the icing. This is done literally by whipping all icing ingredients in another bowl. I’d add the sugar in a bit at a time so it doesn’t become too sweet.
    pre-any sugar.
    pre-any sugar. also, note the amount of bourbon.

    post sugar.
    post sugar.
  7. Assemble the pies. Take the bottom of one cookie, smear it with icing (rubber spatulas are your friend), and attach it the bottom of another cookie.

    A thing of beauty is a joy forever.
    A thing of beauty is a joy forever.
  8. If you want them at room temperature, you’re done. If you want them frozen, cover them individually in Saran wrap and place in the freezer for at least 45 minutes.

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