Pumpkin Whoopie Pies with Maple-Cream Cheese Filling

My fall baking moods seem to take on themes during certain months. Once September hits, I feel like I need to eat and bake with as many apples as possible. Even though they’re available throughout the fall and winter months, I feel a surge in September. It starts to wane towards the end of the month, and then October hits. For me, October is the month of the pumpkin. I know that Thanksgiving is typical pumpkin pie day, but by then I’m already full-on excited and planning for Christmas, so my pumpkin lust starts early. Plus, October gives us Halloween (pumpkin carving and pumpkin seed roasting!) and, more importantly, it gives us “It’s the Great Pumpkin, Charlie Brown”. I’m a sucker for holiday programming and feel very strongly that I should be baking (or, at the very least, eating) something seasonal during every Charlie Brown special or any of the following: Rudolph (the old school one, with the Land of Misfit Toys), Christmas Vacation, Elf or A Christmas Story. Well, October is only a couple of days away so let’s get moving with these whoopie pies!

You may remember me talking about the whoopie pies vs. gobs nomenclature conundrum when I gabbed about s’mores whoopie pies over the summer, but I’ll lay it out there again. It’s weird for me to call these whoopie pies; I grew up calling all cookies of this type ‘gobs’. It’s regional. It’s Pittsburgh. But I also realize it’s a minority. So no matter what you call these, let’s be clear: you need to make and eat these! To celebrate October, of course. And the pumpkins. And Charlie Brown. The cookie-cakes themselves are soft and light and absolutely packed with spicy, seasonal flavors. Your house will smell like Thanksgiving while these are baking. And paired with a maple cream cheese filling? Heaven. An old colleague of mine shared this recipe with me years ago and I’ve been enjoying them ever since. They should become part of your fall baking rotation too!

Two years ago: Cream of Mushroom Soup
Three years ago: Cinnamon Rolls

Pumpkin Whoopie Pies with Maple Cream Cheese Filling

Yield: About 4 dozen assembled whoopie pies (will vary depending on how large you make them)

Prep Time: 15 minutes | Bake Time: 10 to 12 minutes

For the Whoopie Pies:
3 cups all-purpose flour
2 tablespoons cinnamon
1 teaspoon baking powder
1 teaspoon baking soda
1 teaspoon salt
1 teaspoon ground ginger
½ teaspoon ground nutmeg
1 cup granulated sugar
1 cup dark brown sugar
1 cup canola or vegetable oil
3 cups chilled pumpkin puree (canned pumpkin)
2 eggs
1 teaspoon vanilla extract

For the Maple-Cream Cheese Filling:
3 cups powdered sugar
8 ounces cream cheese, at room temperature
4 ounces (½ cup) unsalted butter, at room temperature
3 tablespoons maple syrup
1 teaspoon vanilla extract

1. Preheat oven to 350 degrees F. Line baking sheets with parchment paper or a silicone baking mat.

2. In a large bowl, whisk together the flour, cinnamon, baking powder, baking soda, salt, ginger and nutmeg. Set aside.

3. In a separate bowl, whisk the granulated sugar, the dark brown sugar, and the oil together. Add the pumpkin puree and whisk to combine thoroughly. Add the eggs and vanilla and whisk until combined.

4. Gradually add the flour mixture to the pumpkin mixture and whisk until completely combined.

5. Use a small cookie scoop or a large spoon to drop a rounded, heaping tablespoon of the dough onto the prepared baking sheets, about 1 inch apart.

6. Bake for 10 to 12 minutes, making sure that the cookies are just starting to crack on top and a toothpick inserted into the center of a cookie comes out clean. The cookies should be firm when touched. Remove from the oven and let the cookies cool completely on a cooling rack.

7. To make the filling, beat the butter on medium speed until smooth with no visible lumps, about 3 minutes. Add the cream cheese and beat until smooth and combined, about 2 minutes. Add the powdered sugar a little at a time, then add the maple syrup and vanilla and beat until smooth.

8. To assemble the whoopie pies: Turn half of the cooled cookies upside down. Pipe or spoon the filling (about a tablespoon) onto that half. Place another cookie, flat side down, on top of the filling. Press down slightly so that the filling spread to the edges of the cookie. Repeat until all the cookies are used. Put the whoopie pies in the refrigerator for about 30 minutes to firm before serving.

(As stated above, this recipe came to me from a friend, but as pointed out from a commenter below, it may also be an adaptation from the book Baked: New Frontiers in Baking. I don’t actually own the book, but will likely pick it up in the next few days!)

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