Pumpkin Whoopie Pies with Cream Cheese Filling

Lately my Sunday afternoons have been for baking.  We get up, go to church and afterwards Obed heads out to play flag football with the church league.  This gives me some quiet time alone, which I spend honing my baking skills.  My co-workers encourage this practice since the baked goods usually end up in the office kitchen on Monday morning.  It is my way of trying to curve the Monday morning blues.  Fresh baked goodies can make any Monday morning better.

Pumpkin Woopie Pies

This past Sunday I figured I would attempt the whoopie pie.   I have never had a whoopie pie and to be honest just recently learned about them.  When Obed asked me what I was baking and I told him Pumpkin Whoopie Pies, I got a bit of a raised eyebrow.    He asked why are they called “whoopie” pies and I thought that this was a very valid question because the name is a little odd and well I would like to know for myself.  I did a quick search for the history of the whoopie pie.

Pumpkin Woopie Pies

What I found was that the whoopie pie is originally from New England and a Pennsylvania Amish tradition.  A whoopie pie is two cakey cookies with cream sandwiched in between.  The Amish would make them as a treat from leftover cake batter.  The legend is when children would find them in their lunchbox they would shout “whoopie”, hence the name whoopie pie. (History of the Whoopie Pie)  This explained why Obed and I have never heard of or had a whoopie pie before, being that their aren’t many Amish in the Caribbean.  😀

Pumpkin Woopie Pies

Pumpkin Whoopie Pie

Well let me exclaim that we were deprived!  These whoopie pies are awesomeness!  The cookies are very cakey and moist, and the cream cheese filling is decadent.  This is the perfect fall treat.  The pies are filled will all the fall spices you would imaging, like cloves, cinnamon and ginger.  They are literally little hand held cakes, with frosting on the inside to keep you fingers clean.

Put one in your kids lunchbox today, whoopie!


Pumpkin Whoopie Pies with Cream Cheese Filling
Serves: 24 whoopie pies
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
Cream Cheese Filling
  • 3 cups confectioners’ sugar
  • ½ cup (1 stick) unsalted butter, softened
  • 8 ounces cream cheese, softened
  • 1 tsp pure vanilla extract
  1. Preheat the oven to 350 degrees F. Line two baking sheets with parchment paper.
  2. In a large bowl, whisk together the flour, salt, baking powder, baking soda, cinnamon, ginger, and cloves, set aside.
  3. In a separate bowl or mixer, whisk the brown sugar and oil together until combined. Add the chilled 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.
  4. Using a medium cookie scoop with a release mechanism, drop heaping tablespoons of the dough onto the prepared baking sheets, about 1 inch apart. (If you are baking in batches, refrigerate the dough between batches.) Bake for 10 to 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.
  1. Sift powdered sugar into a medium bowl and set aside.
  2. 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.
  3. Add the confectioners’ sugar and vanilla and beat until smooth. Do not overbeat 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.)
  1. Turn half of the cooled cookies upside down (flat side facing up).
  2. Using the same scoop for the cookies 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.
  3. The whoopie pies will keep for up to 3 days, on a parchment-lined baking sheet covered with plastic wrap, in the refrigerator.
From Baked: New Frontiers in Baking

Note: It is important to chill the pumpkin puree so that the pies keep their shape when you are scooping them out onto the baking sheet. Also if you are baking in batches keep the dough refrigerated between baking.




  1. Sasha says

    Just made these last night for a midnight treat with my boyfriend – UNREAL. thanks for an awesome recipe! Will definitely be making these again!

  2. micaela says

    yum, I’ll be making this for my little boy thanks to you… and since I have no office to take them to tomorrow, I think my neighbors will be very happy.

    How about frituras de calabaza/barriguitas de vieja? will you make some of those, then share your technique? 😉 I’m also an island transplant…

  3. susan says

    I live near Amish country in PA and there is nothing like a freshly baked whoopie pie made by a little old Amish lady with the sweetest smile ever. You’ve got to give chocolate peanut butter ones a try!


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