Pumpkin Chip Whoopie Pies

Oh how the Cinderollies team loves these pumpkin chip whoopie pies! It is one of the greatest times of the year (pumpkin season for those of you who don’t know) so when we saw this pumpkin whoopie pies recipe on Oh Happy Day, we had to share. Enjoy, y’all! We know we will.

Pumpkins Chip Whoopie Pies

Pumpkin Season is officially in full force! I keep seeing it all over the social medias and I’ve been working on recipes with it now for at least a month. We all know pumpkin spice latte season came even earlier this year and ever since we’ve all just been trying to keep up, (spilling your P.S.L. is the actual reason you’re not supposed to wear white after labor day). So now here we are with some fall-ish parties (even if it was 100º here in California last week) and whoopie pies are the perfect thing to finish them off! Pumpkin Chip Whoopie pies, to be exact, with baby chips of chocolate and three buttercream options for the filling: peanut butter, espresso (hiiiii P.S.L. flirty wink), and cream cheese.

Piece of Cake: Pumpkin Chip Whoopie Pies | Oh Happy Day!

Pumpkin Chip Whoopie Pies

Piece of Cake: Pumpkin Chip Whoopie Pies | Oh Happy Day!

For the Whoopie Pies (Makes 32 ‘Cookies’ or 16 Pies):

1 3/4 cups all-purpose flour
1 tablespoon pumpkin pie spice
1/2 teaspoon baking powder
1/2 teaspoon baking soda
1/2 teaspoon salt
1 cup pumpkin puree
1/4 cup vegetable oil
2/3 cup granulated sugar
1/2 cup packed light-brown sugar
1 egg
1/2 teaspoon pure vanilla extract
1/4 cup shaved bittersweet chocolate (Use a vegetable peeler on your favorite bar of chocolate)

Preheat the oven to 350ºF and line two half sheet baking sheets with two of this template each (this is just to help you get those perfect rounds, for pieces of paper total) and a sheet of parchment.

In a medium bowl whisk together the flour, pumpkin pie spice, baking powder, baking soda, and salt. Set aside.

In a larger bowl whisk together the pumpkin, oil, sugars, egg, and the vanilla until combined. Then add the dry ingredients all at once and fold it together just until you don’t see any more flour. Finally, fold in the bittersweet chocolate shavings.

Transfer the batter to a large piping bag, then snip off the end so you have about a 1/2″ opening. Pipe the cookies out onto the baking sheets by holding the piping bag perpendicular to the pan in the center of each circle about 1″ above the baking sheet. Pipe without moving the bag just until the circle fills up, then lift up the bag. Use your finger to push down any batter that’s sticking straight up or acting a fool. Bake the cookies one sheet at a time for 11-12 minutes, or until they’ve spread just a little and they’re firm to the touch. You can also use the “toothpick inserted to see of it comes out clean” method if you want to.

Let the cookies cool completely before removing and assembling the chocolate chip pumpkin whoopie pies (they’ll be a little sticky on the parchment, it’s cool just roll with it).

Piece of Cake: Pumpkin Chip Whoopie Pies | Oh Happy Day!

For the Buttercream:

1/2 cup unsalted butter, softened
2 cups powdered sugar
2 tablespoons heavy cream

For flavor variations, use the above recipe, but add/replace the following ingredients:

Cream Cheese Buttercream:
1/2 cup powdered sugar
4 oz cream cheese
1 teaspoon vanilla bean paste

Peanut Butter Buttercream:
1/3 cup salted peanut butter (smooth or chunky, your preference)

(omit heavy cream)
2 tablespoons cold espresso, strong coffee, or cold brew concentrate.

(Each one will make enough to fill up the whoopie pies on it’s own, so if you want to do multiple options just split a couple recipes in half.)

To make just a plain jane buttercream, sift powdered sugar right into the bowl while using an electric or stand up mixer to beat in butter and heavy cream. Beat until it’s light and fluffy (this should take about a minute). Just make sure you start on low speed until all the powdered sugar’s combined so you don’t wear it like a victorian princess.

To make the cream cheese buttercream: To the buttercream recipe, add the additional powdered sugar, cream cheese, and vanilla bean paste. This one might make a little extra, just throw it in the fridge and use it on french toast or some cupcakes.

For the peanut butter: To the buttercream recipe, add 1/3 cup salted peanut butter, smooth or chunky, your preference.

For the Espresso: Replace the 2 tablespoons of heavy cream in the buttercream recipe with cold espresso, strong coffee, or cold brew concentrate.

To assemble the whoopie pies: Scoop a heaping tablespoon of buttercream on the bottom side of one cookie then place another cookie on top. If you want to make it ahead, make the cookies and leave them on the baking sheet and assemble right before serving, as anything with pumpkin tends to be a little sticky if stacked and sitting.

Piece of Cake: Pumpkin Chip Whoopie Pies | Oh Happy Day!

Pumpkin Chip Whoopie Pies

Piece of Cake: Pumpkin Chip Whoopie Pies | Oh Happy Day!

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