Pumpkin Whoopie Pies

When it comes to parties at the clever girl's school, I generally try to sign up to bring the baked good.  It's just my style.  So I grabbed the chance to bake for the Halloween party last month.  (this is a late post, I agree!)  I imagined little kid-sized whoopie pies with pumpkin filling instead of the marshmallow filling they usually have.  Here is a huge disclaimer, however:  I have never actually eaten a whoopie pie before.  Tragic, I know.  So I am not sure really how they are supposed to taste, nor do I really know what texture they should be.  I'll do my best to describe what I came up with for my pumpkin whoopie pies, and hopefully do these delicious treats justice!


The first recipe I found was from Martha Stewart.  However the comments section fairly universally didn't love the chocolate part.  That's a no go.  I turned to King Arthur Flour and found a chocolate whoopie pie recipe that people claimed tasted like the "real deal".  Since I don't actually know what that is, I went with it!  The recipe describes a whoopie pie as "two saucer-shaped rounds of chocolate cake sandwiched around a marshmallow-y cream filling".  They originally became popular in the New England area and then spread around the US.  They sort of look like an Oreo cookie, but are WAY better....

Start the cake part by beating butter, brown sugar, baking powder, baking soda, salt and vanilla until smooth.  They also suggest adding some espresso powder to this mix, which I agree would bring out the chocolate taste even more, but for a class of 4-yr old kids?  No thank you!  No espresso powder in this batch! 

 Beat in an egg, until smooth.

 Add cocoa powder and stir to combine.

Add flour alternately with milk, beating until nice and smooth.  Mmm, couldn't you just stick your finger in that bowl?  Yum. 

Now, for regular-sized whoopie pies, the recipe says to drop the dough by 1/4-cupfuls onto parchment-lined baking sheets.  For my purposes, I used a tablespoon.  My end result was little cakes about 3-inches in diameter, or maybe a little less.  Bake at 350F for about 12 minutes, or until the tops are set and firm to the touch.  Let cool on the baking sheet for a good while, then transfer to a cooling rack.

In the mean time, make the pumpkin filling!  For this recipe, I basically combined the pumpkin part of the Martha Stewart recipe, with the pumpkin part of a Life Made Simple recipe.  The Life Made Simple recipe added mini-chocolate chips to the filling, which I did not intend to do.  The Martha Stewart recipe was very similar but with less sugar and spices.  So I merged the two and I think I came up with a good solution!

Beat together room temperature cream cheese, room temperature butter, and pumpkin puree until smooth.  Add pumpkin pie spice, salt, and vanilla.  With mixer on low, slowly add confectioners sugar.  The Life Made Simple recipe used 3/4 cup sugar, which I thought would be too much.  The Martha Stewart recipe used 1/2 cup sugar.  After 1/4 cup sugar, I tasted the filling and thought it was not quite there.  I added more sugar a bit at a time and eventually added the 1/2 cup suggested by the Martha Stewart recipe.  Honestly, I think it would be perfect somewhere inbetween 1/4 and 1/2 cup.  Maybe 1/3 cup would be just right.  Adding more sugar actually brought out more of the pumpkin and spice flavors, and I chose to err on the side of possibly too sweet for my tastes since I was baking for 4-year olds.

Anyway, once you have the taste where you want it, spoon or pipe it onto the BOTTOM side of a cake round.  Sandwich another on top and voila!  You have Pumpkin Whoopie Pies!  As you can sort of see in this picture, I assembled each whoopie pie on a piece of plastic wrap.  That way each whoopie pie was it's own separate unit which I thought would travel better to the school and be more fun for the kids.  Plus, this filling is very soft when first made, so you could end up with a gushy mess if you aren't careful!  Once refrigerated, the filling was much better and the whoopie pies were a tad less messy to eat!  Either way, they were delicious and according to the clever girl, her friends loved them!

Pumpkin Whoopie Pies
adapted from several sources, see blog post
CAKES:
1/2 cup butter
1 cup brown sugar, packed
1 teaspoon espresso powder, optional
1 teaspoon baking powder
1/2 teaspoon baking soda
3/4 teaspoon salt
1 teaspoon vanilla extract
1 large egg
1/2 cup Dutch-process cocoa
2 1/3 cups all-purpose flour
1 cup milk

FILLING:
4 oz. cream cheese, room temperature
4 TB (1/2 stick) unsalted butter, room temperature
1/4 cup pumpkin puree
1/4 teaspoon pumpkin pie spice
1/8 teaspoon salt
1/4 teaspoon vanilla
1/3-1/2 cup confectioners sugar, or amount that tastes good to you!

For the cake:
Preheat oven to 350F and line 2 baking sheets with parchment paper.

In a large mixing bowl, beat the butter, sugar, espresso powder, baking powder, baking soda, salt and vanilla until smooth.  Add the egg, beating until smooth.  Add cocoa, and stir to combine.  Add flour and milk alternately, beating until smooth.

Drop the dough by 1/4-cupfuls for large whoopie pies or by the tablespoon for mini-whoopie pies.    Leave plenty of room between each cake, as they will spread.  Bake larger cakes for 15-16 minutes, mini-cakes for 11-12 minutes, or until set and firm to the touch.  Allow to cool partially on the baking sheet, then gently remove from the sheet and finish cooling on a rack.

For the filling:
Beat together the cream cheese, butter and pumpkin puree until smooth.  Add the pumpkin pie spice, salt and vanilla.  With mixer on low, slowly add confectioners sugar until you have reached the sweetness you desire.  Beat until filling is light and fluffy.  Pipe or spoon the filling onto the flat sides of the cakes.  Sandwich the cookies and wrap individually in plastic wrap.  Refrigerate until use.
Printable Recipe

Yum.  Since I have no idea what a "real" whoopie pie tastes like I cannot verify that these are just like the real deal but with a pumpkin filling.  The chocolate part is like small chocolate cakes.  They are not crunchy like a cookie, they are soft like cake.  The filling is soft and has the fall pumpkin/spice that I love.  I think these are a winner!  Some day I will try a bona-fide whoopie pie and know the truth.  Until then, these will be the real deal for me!