Sunny by Design: Pumpkin Whoopie Pies

Nothing says fall to me like pumpkin. I love the smell of it, the taste of it and the wonderful orange, homey look of it. I also love whoopie pies and if you've never tried one they are really a must. I'm not talking about the ones you can buy prepackaged in the store. I'm talking about the cake like cookies that are sandwiched together with any type of wonderful creamy filling in between. There are so many versions of these delightful mouthfuls and I would love to try everyone. But since fall is just around the corner, or is it here already, I had to go with pumpkin and cream cheese. Probably my most favorite flavor combination ever.

The most important thing to know when baking with pumpkin you must use canned pumpkin puree and not the canned pumpkin pie mix. The canned pumpkin pie mix is already seasoned with spices for baking pie. You want pumpkin that is plain with no spices already added. If you are really high speed you can bake your own pumpkin and puree the pulp yourself. That's a little too much work for me, so the can works just fine.

When I decided to make these I knew I wanted a whoopie pie that was moist, somewhat spongy and a little on the flatter side. Making it easier to eat. Most recipes I came across showed a cookie with a cracked top and I prefer a smooth bouncy moist cookie, that feels more like cake. I used the recipe I found on Martha Stewart.com by Matt Lewis of Baked Bakery. The first time I baked the cookie it did crack on top and it was a little too dense for me, so I added a little milk to smooth out the batter and tweaked a few other ingredients to create the lovely, moist, cake like cookie that I was looking for.

Here is what you will need...

Ingredients:

Pumpkin Whoopie cookies
Adapted from recipe by Matt Lewis of Baked bakery.
(this makes about 48 cookies that can be assembled into 24 smallish whoopie pies)
1 cup vegetable oil
1 cup granulated sugar
1 cup light brown sugar
3/4 cup milk
2 large eggs
3 cups pumpkin puree
1 teaspoon vanilla extract
3 cups all-purpose flour
1 Tablespoon cinnamon
1 teaspoon nutmeg
1/4 teaspoon cloves
1 teaspoon baking powder
1 teaspoon baking soda
1 teaspoon salt

Cream Cheese Filling
4 cups powdered sugar
1/2 cup unsalted butter (softened)
8 oz cream cheese (softened)
1 teaspoon vanilla

First preheat the oven to 350 degrees and cover your baking sheets with parchment paper or waxed paper.

Next sift the flour, cinnamon, nutmeg, cloves, baking powder, baking soda, and salt into a large bowl and then give it a gentle whisk until combined. Set the dry mixture aside.

In another bowl with an electric mixer or standing mixer, mix the oil and sugars together.

Then add the eggs one at a time and mix until combined. After that add the milk, vanilla and pumpkin and mix until they are well incorporated. Look at that pretty color.

Next add the dry ingredients to the wet ingredients 1/3 at a time, mixing until just combined after each addition. Be careful not to over mix it here. You just want to mix until the batter is smooth with no lumps.

Using a small ice cream scoop or a large spoon drop the dough onto the parchement lined baking sheet a generous 1 inch apart. Once they are on the sheet take the back of the scoop or a spoon and spread them around just a tiny bit to even them out. This will ensure the cookies stay flat instead of puffed up. I really like a flatter cookie/cake because it makes them much easier to eat when they are sandwiched together. Plus you get a better cookie to filling ratio. That's so important.

Bake the cookies for 12 minutes or until they are firm to the touch. Let them sit for about 5 minutes and then move the cookies from the pan to a wire rack to finish cooling.

While they are cooling you can make the filling, which is very similar to my cream cheese frosting. Wait it is my cream cheese frosting recipe.

For the filling first sift the powdered sugar into a bowl and set aside. With an electric mixer or a stand mixer beat the soft/room temperature butter and the soft/room temperature cream cheese until smooth, about 3 minutes. Add the powdered sugar 1/2 at a time mixing very slowly at first then turn up the speed to medium to finish it off. Lastly add the vanilla and mix well. The final mixture should be smooth with no lumps and soft enough to spread but stiff enough to stay in place. If your mixture is too gooey then place in the fridge for 30 minutes to an hour to let harden a bit.

Before assembling the pies match similar cookies together and place them in stacks of two on a sheet of waxed paper or parchment paper. It’s kind of amazing that if one cookie has an odd shape chances are it has a match.

Once they are all matched up place your filling in a piping bag fitted with a large star tip
or a large round tip or just take a spoon and pipe or dalop the filling onto the flat side of one of each of the cookie pairs.

Once the filling is in place put the cookie on top and press gentley to spread the filling out and you're done. If these are a little soft and hard to manage, store them in the fridge for about an hour to harden up. The filling gets soft while you are working with it and it helps to keep it cold. These store nicely in the fridge for up to 4 days. So they can be made a couple days in advance if need be.