Matt & Renato couldn't have said it better "try as we might, we were never huge fans of the traditional whoopie pie." Their version below was listed as one of the top 100 tastes of 2007 by Time Out New York. Their whoopie pie would satisfy any midnight craving, with its soft, cake like cookie and chilled cream cheese filling.
It was the first day of Fall today. This is my favorite time of year and seeing all of the pumpkins displayed at our local farms put me in the mood to make these babies! So here they are and maybe, just maybe, they will inspire nature to bring on the typical fall weather for us!
These were easy and fun to do with my 6 year old daughter. A word of warning: don't assume you have enough of the spices on hand...I usually have small containers and they use take tablespoons rather than teaspoons here. Quick and painless to make so go ahead....try them! You won't be sorry...ok, maybe your hips will be, but your taste buds won't! Ha!
FOR THE PUMPKIN WHOOPIE COOKIES
3 cups all-purpose flour
1 tsp salt
1 tsp baking powder
1 tsp baking soda
2 Tbs cinnamon
1 Tbs ginger
1 Tbs cloves
2 cups firmly packed dark brown sugar
1 cup vegetable oil
3 cups chilled pumpkin puree
2 large eggs
1 tsp pure vanilla extract (I used vanilla paste since it was being baked)
FOR THE CREAM CHEESE FILLING
3 cups confectioner's sugar
1/2 cup (1 stick) unsalted butter, softened
8 oz cream cheese, softened
1 tsp pure vanilla extract
MAKE THE PUMPKIN WHOOPIE COOKIES
Preheat the oven to 350 degrees F. Line two baking sheets with parchment paper.

In a separate bowl, whisk the brown sugar and oil together until combined. Add the pumpkin puree and whisk to combine thoroughly. Add the eggs and vanilla and whisk until combined.
Sprinkle the flour mixture over the pumpkin mixture and whisk until combined.
Use a small ice cream scoop (I used a cookie dough scoop) with a release mechanism to drop heaping tablespoons of the dough onto the prepared baking sheets, about 1 inch apart. Bake for 10-12 minutes, until the cookies are just starting to crack on top and a toothpick inserted into the center of a cookie comes out clean. Remove from the oven and let the cookies cool completely on the pan while you make the filling.
In the bowl of an electric mixer fitted with the paddle attachment, beat the butter until it is completely smooth, with no visible lumps. Add the cream cheese and beat until combined.
Add the confectioners' sugar and vanilla and beat until smooth. Be careful not to over beat the filling, or it will lose structure. (The filling can be made 1 day ahead. Cover the bowl tightly and put it in the refrigerator. Let the filling soften at room temperature before using).
ASSEMBLE THE WHOOPIE PIES
Turn half of the cooled cookies upside down (flat side facing up).
Use an ice cream scoop or a tablespoon to drop a large dollop of filling onto the flat side of the cookie. Place another cookie, flat side down, on top of the filling. Press down slightly so that the filling spreads 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 up before serving.
The whoopie pies will keep for up to 3 days, on a parchment-lined baking sheet covered with plastic wrap, in the refrigerator.
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