Pumpkin Whoopie Pies with Cream Cheese Filling

Get your mind out of the gutter.

Really.

We’re talking about making whoopie pies here, not making whoopie.

If you’ve never heard that expression, bless your innocent little heart. Resist the temptation to google it. I can’t be responsible for corrupting you.

(You googled it, didn’t you?)

Now that we have that uncomfortable discussion out of the way…

Whoopie pies.

They’re not actually pies. I’d say that “fluffy, maple-y cream cheese filling sandwiched between two moist, melt-in-your-mouth pumpkin cake cookies” is a more accurate description.

You should probably make these as bite-size whoopie pies. That way, you won’t feel as guilty after consuming 3 or 4 of them. And the smaller they are, the easier it is to eat them covertly.

Just make sure you don’t get cream cheese all over your face. Because then everyone will know. The questions will start flying. And you’ll have to explain yourself.

That’s what you get for making whoopie. Pies.

Pumpkin Whoopie Pies with Cream Cheese Filling
Recipe from Matt Lewis of Baked Bakery

Active time:  30 minutes
Start to finish: 1 hour
Makes 12 large pies or 24 bite-sized ones

Ingredients
For the pies
3 cups all-purpose flour
1 teaspoon salt
1 teaspoon baking soda
1 teaspoon baking powder
2 tablespoons ground cinnamon
1 tablespoon ground cloves
1 tablespoon ground ginger
1 cup vegetable oil
2 cups dark brown sugar
3 cups pumpkin puree, chilled
1 teaspoon vanilla
2 eggs

For the cream cheese filling
1/2 cup (1 stick) unsalted butter, softened
1 8-oz package cream cheese, softened
3 cups powdered sugar
3 tablespoons maple syrup or 1/2-1 teaspoon maple extract
1 teaspoon vanilla

Directions

For the cookies
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.
  • Using a small ice cream scoop, drop heaping tablespoons of batter onto prepared baking sheets, about 1 inch apart. (For bite-size pies, use half-tablespoons of batter.) Try to keep your batter drops as circular as possible. 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 10-14 minutes . Let cool completely on pan.

    For the filling
    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 powdered sugar, vanilla, and maple syrup (or extract); 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.)

    Assemble the whoopie pies
    Line a baking sheet with parchment paper and set aside. Transfer filling to a disposable pastry bag and snip the end. When cookies have cooled completely, pipe 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 cookies at least 30 minutes before serving. Can be refrigerated up to 3 days.

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