Oatmeal Whoopie Pies with Raspberry, Cinnamon and Sugar Filling

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While Zach is away, Justine will bake! I’ve really been craving something sweet lately, and store bought cookies and candies just haven’t been doing the trick. Sometimes you just crave a homemade cookie, and sometimes you crave homemade cookie with a cream filling! This recipe is like your everyday, old whoopie pie gone crazy! It’s packed full of sugar and spice and everything nice, and it will be sure to curb that craving for something sweet. The oatmeal cookies are good all by themselves, but the addition of a raspberry, cinnamon and sugar filling just makes this cookie all the more better! I hope you all enjoy it and enjoy making it as well!

Again, I decided not to pair this recipe with a beer. Of course, you could pair it with anything you like. I think it goes well with a rich cup of coffee, so that is exactly what I decided to pair it with. There is so much flavor and goodness packed into this cookie, that I feel a beer pairing wouldn’t do it justice and would probably just take away from it’s deliciousness.

Please enjoy!

Cream Mixture!

Ready for the oven!

NOW they are ready for the oven!

Cookies Cooling!

Raspberry Cream Mixtures!

Ready to eat! Yum!

Oatmeal Whoopie Pies with Raspberry, Cinnamon and Sugar Filling
Prep Time
40 min
Cook Time
1 hr
Total Time
1 hr, 40 min


  • 3/4 cup of butter, softened
  • 1/2 cup shortening
  • 2 cups light brown sugar
  • 2 large eggs
  • 1/2 cup buttermilk
  • 1 1/2 teaspoon vanilla extract
  • 1 1/2 cup all purpose flour
  • 1 teaspoon baking soda
  • 1/4 teaspoon salt
  • 1 teaspoon baking powder
  • 1 teaspoon FRESH ground ginger
  • 1 teaspoon FRESH ground nutmeg
  • 1 tablespoon cinnamon
  • 2 cups quick oats
  • 2 to 3 cups Raspberry, Cinnamon and Sugar Filling
  • 1 cup butter, softened
  • 4 cups powdered sugar
  • 1 tablespoon cinnamon
  • 1 teaspoon vanilla extract
  • 1/4 cup heavy cream
  • 3/4 cup frozen raspberries, roughly chopped


  • Preheat your oven to 350 degrees and grease two baking sheets with butter or non-stick spray.
  • In a stand mixer, using the whisk attachment, beat the butter, shortening, and brown sugar together until creamy. One by one, add the eggs individually, and beat until well incorporated. Then add the buttermilk and vanilla extract, and beat until just combined. Set aside, you will be coming back to this mixture in a minute.
  • In another bowl, sift together the flour, baking soda, baking powder, salt, cinnamon, ginger, and nutmeg.
  • Next, you are going to fold the "dry" ingredients into the "wet" ingredients. Do this with a rubber spatula, and be sure to get every nook and cranny. Make sure there are no lumps, and everything is smooth.
  • Next you are going to fold in the oats with your rubber spatula. Do this in 1/2 cup batches, and do it slowly. Once everything is combined, start forming your cookies and placing them on the cookie sheet. For this recipe, I suggest using a large ice cream scoop. You want to have large cookies because you will eventually be making whoopie pies out of them. I suggest only placing 6 cookies per cookie sheet, at about 2 inches apart. They will grow!
  • Bake for 12 to 15 minutes, and remove from the oven. Let sit on the sheet for a minute or two, and then remove and place on cooling rack so that they cool COMPLETELY! Once they have cooled, scoop about 1/4 cup of filling onto one of the cookies and then top with another. Refrigerate until ready to serve and then ENJOY!
  • For the filling, in your stand mixture, with the whisk attachment, whip the butter until creamy. In 1 cup increments, add the powdered sugar. Do this until the mixture is smooth and creamy. Next add the cinnamon, vanilla extract, and heavy cream, and cream together until the mixture is nice and fluffy and has taken on that frosting "consistency." Then, you are going to VERY GENTLY fold in the raspberries. Your filling will start to turn a pinkish color, but this is ok. Cover and immediately refrigerate for 45min to 1hr, then it is ready for use in your Oatmeal Whoopie Pies!


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