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Copycat Oreo Cakesters (Oreo Whoopie Pies)

Oreo Cakesters are making a comeback – in your kitchen, that is. These Oreo Whoopie Pies are soft and moist cake-like cookies stuffed with fluffy vanilla filling, made completely from scratch. A family favorite copycat recipe!

A stack of three Oreo whoopie pies on a white plate.

The latest obsession around here: these Oreo whoopie pies. Is it a cookie? Is it cake? Let’s just call it a cake-like cookie, and we’ve been devouring them. Just having these whoopie pies in the house is causing a milk shortage from all the munching going on.

Besides, in honor of Oreo Cakesters making their grand return in 2022 (after a 10-year hiatus!), why not celebrate with a homemade tribute. Making these soft, fluff-filled cookies from scratch has the whole family reliving the glory days of these vintage lunchbox snacks. An Oreo-naissance, if you will.

These fluffy, moist chocolate cookie sandwiches are surprisingly simple to make. Just like the original, my homemade Oreo whoopie pies taste like a cookie but have that soft, tender mouthfeel of a cake. Like taking a bite of a vanilla cloud wrapped in a hug of chocolate. It’s truly something special!

Two halves of an Oreo whoopie pie revealing the layers of chocolate cookie and vanilla cream filling.

What Are Oreo Cakesters?

Oreo Cakesters are essentially the Nabisco answer to a whoopie pie. Also known as Gobs (if you happen to be from Pittsburgh), whoopie pies are mini cake-like cookie sandwiches with a creamy filling often made from marshmallow or frosting. You’ll sometimes find variations like pumpkin whoopie pies, depending on where you live. 

In the case of an Oreo Cakester, this involves a soft and fudgy chocolate snack cake filled with fluffy Oreo vanilla creme. Cakesters were a popular treat right up until Oreo discontinued them in 2012. It was a dark day for lunchboxes.

Luckily, making these nostalgic cookies at home isn’t so hard. If you never had the privilege of trying a classic Oreo Cakester, join me in making this soft and creamy, melt-in-your-mouth copycat.

The ingredients for Oreo whoopie pies.

Recipe Ingredients

Below you’ll find an overview of what you’ll need for the chocolate cookies as well as the vanilla filling. Don’t forget to refer to the recipe card for the full ingredient amounts.

For the cookies

  • All-purpose flour
  • Dark cocoa powder – Dutch processed cocoa powder gives the chocolate cookies the fudgiest taste texture.
  • Baking soda and salt – Baking soda for a leavening and salt to enhance the flavors.
  • Butter – I recommend baking with unsalted butter, it’s the easiest way to ensure the cookies don’t come out overly salty!
  • Sugar – A combination of granulated sugar and brown sugar for the perfect amount of sweetness and moisture. 
  • Egg
  • Vanilla – Pure vanilla extract or an equal amount of vanilla bean paste, as opposed to imitation.
  • Buttermilk – Buttermilk brings softness and richness (plus a bit of tang) to these cakey chocolate cookies.

For the filling

  • Butter – Make sure your butter is at room temperature to make it easier to combine.
  • Icing sugar – Also called powdered sugar, for a smooth texture.
  • Clear vanilla extract – Here I recommend using clear vanilla extract to preserve that authentic, bright white color of the vanilla filling. Regular vanilla extract or paste will impact the color – the taste will be the same, though.

How to Make Oreo Whoopie Pies

The prep for the chocolate cookies takes a bit of time, but then they bake up lightning quick in the oven. Afterwards it’s smooth sailing (or filling) before the sandwiches are done. Small effort, major reward! Let’s get going on these whoopie pies:

Prep your tools. While the oven preheats, line two cookie trays with parchment paper.

Make the cookie dough. First, mix the flour, cocoa, and dry ingredients, and then the wet ingredients separately. Make sure to beat the butter and sugar nice and fluffy before adding in the egg, vanilla, and buttermilk, scraping down the sides of the bowl along the way. Next, add the dry ingredients into the wet ingredients in batches. Be careful to not overmix!

Portion out the cookie dough. Once you have a dough that’s thick and dense, portion out a half teaspoon of cookie dough and form it into a bowl shape. Place the shaped dough onto your baking sheet and then repeat. You’re aiming for about 38 cookies, for 19 cookie sandwiches. Don’t forget to leave enough space in between the cookies. 

Bake. Place the cookies into the oven at 325°F. In about 7 minutes, they should be set. The center of the cookie should be soft to the touch – try not to overbake, or you’ll end up with dry, crunchy cookies. Next, leave the cookies to cool on the tray before preparing the vanilla filling.

Make the filling. Cream the butter with the icing sugar for a few minutes to get it super smooth and creamy, then add the vanilla extract. 

Fill the cookies. Lastly, it’s time to assemble your whoopie pies. Ensure that the cookies are fully cooled, then pipe the filling into the centers of half the cookies. Top with the remaining cookie halves. Transfer the sandwich cookies to an airtight container to chill in the fridge for an hour, and then serve! These cookies and a glass of milk are the definition of a match made in heaven.

Two Oreo whoopie pies stacked on a white plate, with a third whoopie pie cut in half to reveal the chocolate cookie and vanilla filling layers.

Tips for Success

Some helpful reminders when making these copycat Cakesters:

  • If the cocoa powder is clumpy. If your cocoa powder has lumps in it, sift it before adding it to the dry ingredients. The same goes for the flour, and the powdered sugar in the filling.
  • Don’t overmix. This applies when mixing the wet ingredients, and when adding in your flour mixture. Over mixed dough will yield tough, overly dense cookies.
  • Account for spreading. The dough will puff up and spread as it bakes (which is the goal). Be sure to leave a few inches of space between each cookie on the baking sheet, and work in batches if needed.
  • Use clear vanilla extract for the filling. For that bright white look, stick with clear extract in the vanilla filling. The seeds in vanilla bean paste will be visible. 
  • Don’t stack the cookies. These little sandwiches are stacked enough as it is! Avoid stacking the whoopie pies when storing them in the fridge. See below for more storage tips.
Close up of one half of an Oreo whoopie pie on a countertop.

How to Store Homemade Whoopie Pies

These whoopie pies should be kept in the fridge, in an airtight container. They tend to get overly soft and the filling gets slippery when left at room temperature.

Can I Freeze These?

Whoopie pies can be stored for up to 2 months in the freezer. I recommend freezing the cookie sandwiches solid on a baking sheet before transferring them to a container or freezer bag. Thaw the cookies in the fridge before serving.

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Copycat Oreo Cakesters (Oreo Whoopie Pies)

A stack of three Oreo whoopie pies on a white plate.
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These Oreo whoopie pies are soft and moist cake-like cookies stuffed with fluffy vanilla filling. A family favorite copycat of Oreo Cakesters, made completely from scratch!

  • Author: Rustic Family Recipes
  • Prep Time: 40 minutes
  • Cook Time: 7 minutes
  • Total Time: 47 minutes
  • Yield: 19 cookies
  • Category: Cookies
  • Method: Oven
  • Cuisine: American

Ingredients

For the cookies

  • 1 ⅓ cup all-purpose flour
  • ⅔ cup dark cocoa powder
  • 1 ½ tsp baking soda
  • ¼ tsp salt
  • ½ cup softened unsalted butter
  • ⅔ cup granulated sugar
  • ⅓ cup brown sugar
  • 1 large egg
  • 1 tsp vanilla extract
  • 1 ½ tbsp buttermilk

For the filling

  • ¼ cup butter at room temperature
  • 1 cup icing (powdered) sugar
  • 1 tsp clear vanilla extract

Instructions

Prep your tools. Preheat the oven to 325°F. Line two cookie trays with parchment paper and set aside.

Combine the dry ingredients. In a medium bowl whisk together: flour, cocoa powder, baking soda and salt.

Combine the wet ingredients. Fit a stand mixer with a paddle attachment. Cream the butter with the sugars until light and fluffy (approx. 5-7 minutes on medium-high speed). Scrape down sides of the bowl 3 times in the process.

Add the egg, vanilla, buttermilk and mix for 30 seconds, scrape down sides of the bowl and mix just until combined. Do not over mix.

Mix the dry ingredients into the wet ingredients. Add the flour mixture in two batches, mixing until incorporated and scraping down the bowl in between the additions. The dough should be thick and dense.

Portion out the cookie dough. Scoop out ½ tbsp (0.5 oz) of the dough, shape into a bowl and drop on the cookie sheet.

Repeat with the remaining dough, dropping it a few inches apart. You should get 38 cookies, which will make 19 cookie sandwiches.

Bake. Bake at 325°F for 7 minutes. The cookies should still be slightly soft to the touch in the middle at the end of the baking time. Leave them to rest and cool completely on the baking trays.

Make the filling. To make the filling, cream the butter with icing sugar on medium speed in a bowl of a stand mixer fitted with the paddle attachment or an electric hand mixer. This should take approx. 5 minutes. Add vanilla extract and mix for a few seconds just until combined. The filling should be smooth and creamy.

Fill the cookies. Place the filling in a piping bag, and pipe out a portion onto the center of each of the 19 cookies. Cover with the top cookie and gently press down. Place the cookies in an airtight container and refrigerate for an hour before serving, or serve slightly soft!

Notes

  • The cookie dough will spread as it bakes so make sure to leave at least a few inches of free space between each dough ball on the cookie sheet.
  • Use clear vanilla extract for the filling. Given the color of the filling, the seeds of vanilla bean paste will be clearly visible.
  • The cookies should be stored in the fridge, in an airtight container.

Keywords: whoopie pie recipe, oreo dessert, sandwich cookies, oreo cakesters

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