Baked Brooklyn's Pumpkin Whoopie Pies (and Nutella Hot Chocolate )

My husband's birthday was coming up fast and I needed to pull a plan together. Absolutely nothing was going to top his 35th birthday weekend, which was last year. To celebrate the special day the last time around I really pulled out all the stops: Park Avenue Autumn for brunch, Nara at the Asia Society in the afternoon, Daniel for dinner (oui!) and tickets to Yankee post-season baseball (props to my mom for getting the tickets). The next day we went to Diner for brunch, Spa Castle for relaxation and then apple picking Upstate. It was great and it was going to be hard to replicate anything like that this year...especially since there's an 11 week old in the house and we haven't secured a babysitter.
I picked up a gift and decided to go with something more muted-- a little more family friendly-- and very local. I went with brunch in our house. Of course the best gift I gave my husband was the gift of sleep. He slept till 11:00 AM and woke up to a birthday brunch.  
I made a three egg omelette with Gruyere cheese, topped with homemade salsa verde, and some breakfast potatoes on the side.  It was delicious. But the piece de resistance was the pumpkin whoopie pie from Baked, Brooklyn. Yes, *that* whoopie pie-- the one that won top 100 tastes of 2007 by Time Out New York.
Baked is one of my most favorite bakeries (miss you!), and this recipe is from their cookbook Baked: New Frontiers in Baking.  
If you really want to go a little over the top,  pair it with nutella hot chocolate.  It's perfect for a chilly fall night.  It's lip-smacking good! 
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Baked Brooklyn's Pumpkin Whoopie Pies (Courtesy of Baked: New Frontiers in Baking)
3 cups all-purpose flour
1 teaspoon salt
1 teaspoon baking powder
1 teaspoon baking soda
2 tablespoons cinnamon
1 tablespoon ground ginger
1 tablespoon ground cloves
2 cups packed dark-brown sugar
1 cup vegetable oil
3 cups chilled pumpkin purรฉe
2 large eggs
1/2 teaspoon vanilla extract
3 cups confectioners sugar
1/2 cup (1 stick) unsalted butter, softened
8 ounces cream cheese, softened
1 teaspoon vanilla extract
Preheat oven to 350ยฐF. Line two baking sheets with parchment paper.
In a large bowl, whisk the flour, salt, baking powder, baking soda, cinnamon, ginger, and cloves together and set aside.
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 completely combined.
Use a small ice cream scoop with a release mechanism to drop heaping tablespoons of the dough onto prepared baking sheets, about one inch apart. Bake for 10 to 12 minutes, until the cookies are just starting to crack on top and a toothpick inserted into the center of the cookie comes out clean. Remove from the oven and let the cookies cool completely on the pan while you make the filling. 
(I used a whoopie pie pan so the domes were very smooth and round.  I think you get a more 'rustic' cookie, if I can call it that, when you put dough on baking sheets.) 
For the Cream Cheese Filling
Sift the confectioners' sugar into a medium bowl and set aside.
In the bowl of an electric mixer fitted with paddle attachment, beat the butter until it's 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 overbeat the filling, or it will lose structure. (The filling can be made one day ahead. Cover the bowl tightly and put it in the refrigerator. Let the filling soften at room temperature before using.)
Assembling 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 whooopie 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.
Baked Note: Make sure you chill the pumpkin puree thoroughly before making this recipe.  The chilled puree will make your whoopie pies easier to scoop. 

Nutella Hot Chocolate (Courtesy of Real Mom Kitchen)
  • 4 cups whole milk
  • 1/2 cup Nutella
  • mini marshmallows or whipped cream
In a medium sauce pan over medium-low heat, whisk together milk and Nutella until the Nutella is melted and milk gets nice and warm. Serve in mugs and top with marshmallows or whipped cream. Makes 4 servings.
This can be made ahead of time, cooled, and stored in the fridge.  Reheated on the stove or microwave in individual mugs.  If microwaving, reheat each cup for about 1 minute.