Pumpkin Whoopie Pies with Maple Cream Cheese Frosting

Pumpkin-Whoopie-Pies-5Baking is hard.

Recently, I had a run-in with a three-layer cake and a time constraint. Confectioners sugar was my enemy for about 15 long minutes. I don’t really want to talk about it…

However! Let’s do talk about the fun little world of the Whoopie Pie! Basically, the Whoopie Pie is like a little cake – like cupcakes but less messy and much easier to eat. They are nothing like a pie, so the name is a little deceiving. Perhaps they should be called Little Hand Cakes..? Naaahh… Whoopie Pie is so much more fun to say and sometimes it’s fun to say fun things.


Pumpkin-Whoopie-Pies-6This is the first time I’ve ventured into the Whoopie Pie world and I’m so glad I did. Not only are they simple to make, but this recipe yields a lot of pies and I can see myself exploring many other flavors in this delightful little Whoopie Pie world.

Recently, just for fun, I entered these Pumpkin Whoopie Pies in a baking contest. As the baking contest took place during a Fall Festival, naturally, the criteria was simple: use pumpkin as the main ingredient.

Pumpkin-Whoopie-Pies-2These spiced and delicious Pumpkin Whoopie Pies took home the “Most Unique” prize, and for all their hard work on the runway these spiced and delicious Pumpkin Whoopie Pies are getting published on Figs & Feta. I think they deserve it. Don’t you?

Interesting fact about pumpkins and the country of Greece: In Greece, the pumpkin season’s peak is during the summer months, as opposed to the fall months here in the United States. In July and August outside of Athens along remote countryside roads you will find road-side stands flooded, and I mean flooded, with pumpkins and gourds. On my visits to Greece, I always loved seeing the bright orange, yellow pile of pumpkins decorate the light brown, dry dirt roads. Funny that their time to shine is during the summer though – Pumpkin Whoopie Pie with your karpouzi (Kar-pouzi – watermelon) anyone? ;)

Pumpkin-Whoopie-Pies-7Since Figs & Feta is a Greek Food Blog you may be asking yourself what makes this recipe for Pumpkin Whoopie Pie, Greek? Here’s my answer, as only a Greek would answer:

1) The name pumpkin originated from the Greek word for “large melon” which is “pepon.”

2) Need I go on?

3) I am Greek, and I made these with my Greek hands, so therefore they are Greek. ;)

4) Yes, pumpkins exist in Greece (see above).

5) These treats are award-winning crowned at a Greek Orthodox Christian Church festival, so not only are they Greek, but they are blessed. ;)



Years ago during a 30-Minute Meal episode, Rachael Ray advised
Years ago during a 30-Minute Meal episode, Rachael Ray advised “Get pumpkin pie spice at the store during the fall!” She’s right- it’s hard to find this delicious spice any other time during the year so snatch some up! Also, a few years back Real Simple Magazine rated canned pumpkin. Market Pantry brand came out on top. You can pick some up at Target Stores.


For the Whoopie Pies:

3 cups all-purpose flour

1 1/2 tablespoons cinnamon

2 teaspoons pumpkin pie spice

1 teaspoon baking powder

1 teaspoon baking soda

1 teaspoon salt

1 cup granulated sugar

1 cup dark brown sugar

1 cup canola or vegetable oil

3 cups canned pumpkin (about 1 ½ cans)

2 eggs

1 teaspoon vanilla extract


For the Maple-Cream Cheese Filling:

3 cups powdered sugar

8 ounces cream cheese (1 package), at room temperature

2 sticks (½ cup) unsalted butter, at room temperature

5-6 tablespoons maple syrup

1 teaspoon vanilla extract


  1. Preheat oven to 350 degrees. Line baking sheets with parchment paper.
  2. In a large bowl whisk together the flour, cinnamon, pumpkin pie spice, baking powder, baking soda, salt. Set aside.
  3. In a stand mixer with the whisk attachment, whisk together the oil, granulated sugar, the dark brown sugar. Add the pumpkin puree and whisk to combine thoroughly. Add the eggs and vanilla and whisk until combined.
  4. Gradually add the flour mixture to the pumpkin mixture and whisk until completely combined.
  5. Use a small cookie scoop or a large cookie scoop, (depending on how large you want the whoopie pies to be) drop a rounded, heaping scoop of the dough onto the prepared baking sheets, about 1 inch apart. These do not expand, so however large you drop them onto the cookie sheet that’s how large your whoopie pies will be.
  6. Bake for 12-14 minutes. The cookies should be firm when touched. Remove from the oven and let the cookies sit on the pan for about 2 minutes. Remove and cool completely on a cooling rack.
  7. Prepare the filling: In a stand mixer with the paddle attachment, mix the butter on medium speed until smooth. Add the cream cheese and mix until smooth and combined, about 2 minutes. Add the powdered sugar a little at a time, then add the maple syrup and vanilla and mix until smooth.
  8. To assemble the whoopie pies: Turn half of the cooled cookies upside down. Use a small cookie scoop to drop about 1 tablespoon of the cream cheese filling onto the flat side. 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. Put the whoopie pies in the refrigerator for at least 30 minutes to firm before serving.

Recipe adapted from the cookbook Baked: New Frontiers in Baking. Baked is located in Red Hook, Brooklyn, NY.


©2014 by Alexandra Salidas Roll, Figs & Feta, LLC.

Recipe and photos by Alexandra Salidas Roll of Figs & Feta, LLC.  Please do not reprint this recipe without permission.  If you would like to feature this recipe on your blog or site, please rewrite the method of preparation and link your post to this one as the original source.  Thank you!

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