Pumpkin Whoopie Pies

Pumpkin time is here! Duh, I’m like weeks late on that whole phenomenon, but I barely know what day it is now that our puppy Piper rules the world over here, so you can’t blame me. I don’t get quite as excited as everyone else about pumpkin season, mostly because I don’t care so much for the sweet PSL (shocker!) and canned pumpkin kind of makes me gag. But I’d be banned as a blogger if I didn’t share at least one pumpkin recipe a year, so here we are. Honestly though, I absolutely LOVED these – totally worth dealing with all that mushy orange stuff :)

Pumpkin Whoopie Pies4-8 copy

I saw whoopie pies decorated like these a few years ago by Your Cup of Cake and always remembered how cute they were. Not only are they made with real pumpkin, they look like little pumpkins too! Thanks to tootsie roll stems and greens icing vines, they’re as festive as they taste. You could even dye the frosting center orange to really complete the full pumpkin look, but I wanted to keep things somewhat classic with a simple white cream cheese frosting. The combination is classic for a reason -omgsososogood!!

Pumpkin Whoopie Pies2-30 copy

What’s great about whoopie pies for me is that the ratio of cake to frosting is just perfect, at least compared to cupcakes. Of course these pumpkin spice latte cupcakes from a few years ago are phenomenal, but I love whoopie pies because you get a lot of frosting with every single bite. I made these mini so they’re really only 2 or 3 bites total, but every bite is a perfect combination of spicy pumpkin and creamy, tart cream cheese frosting. The tootsie roll doesn’t really go in terms of flavors or texture, but the look was just too cute to pass up. Now who’s going pumpkin picking this weekend??

Print Recipe
Save Recipe

Pumpkin Whoopie Pies

Recipe adapted from Annie's Eats

Yield: About 40 mini whoopie pies


for the pumpkin whoopie pies:

3 cups all purpose flour
1 tsp salt
1 tsp baking soda
1 tsp baking powder
2 tbsp cinnamon
1-1/2 tsp pumpkin pie spice
1 cup granulated sugar
1 cup brown sugar, packed
1 cup vegetable oil
3 cups pumpkin puree
2 eggs
1 tsp pure vanilla extract

for the cream cheese frosting:

3 cups powdered sugar
1/2 cup unsalted butter, at room temperature
8 oz cream cheese, cold
2 tsp pure vanilla extract

for decoration:

20 mini tootsie rolls, cut in half
Green food coloring


for the pumpkin whoopie pies:

Preheat the oven to 350 degrees and line two large baking sheets with parchment paper or Silpat mats. In a large bowl, whisk together the flour, salt, baking soda, baking powder, cinnamon, and pumpkin pie spice.

In another bowl, combine the sugar and oil. Add the pumpkin puree and mix until thoroughly combined. Add the eggs and vanilla and whisk until evenly incorporated. Slowly add the flour mixture to the pumpkin mixture and fold in until evenly combined.

Transfer the whoopie batter to a pastry bag fitted with a large plain round tip, or just use a ziploc bag with the corner snipped off. Pipe small circles (about 1.5" in diameter) of dough onto the prepared baking sheets, leaving about 1" in between each one.

Bake for 10-12 minutes, or until the cookies are just starting to crack on top and a toothpick inserted into the center comes out clean. Allow whoopie pies to cool on the pan for 5 minutes, then transfer to a wire rack to cool completely. Repeat with remaining batter until all of the whoopie pie dough is used.

for the cream cheese frosting:

In the bowl of an electric mixer, beat together the butter and cream cheese on medium-high speed until fluffy, about 2-3 minutes. Slowly add the powdered sugar and continue to beat for another minute. Add the vanilla and mix again. Set aside about 1/2 cup of the frosting in a separate bowl and add a drop or two of green food coloring.

Pair up the whoopie pie cookies by size and load a pastry bag fit with a large round tip with the white cream cheese frosting. Pipe the filling on the flat side of one cookie from each pair, and sandwich together with the other cookie.

to decorate:

Place a halved tootsie roll into each whoopie pie. Don't do this step too far in advance or you'll notice the tootsie roll will kind of "melt" a bit. I recommend waiting to do this until the day you plan on serving them. Put the green frosting in a bag fit with a small round tip and pipe a swirl of vines on the side of each tootsie roll. Store in the refrigerator until ready to serve.

Pumpkin Whoopie Pies-38 copy

    Pin It

Leave a Comment