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Oatmeal Whoopie Pies with Baked Apples and Cream Cheese Buttercream

October 20, 2017

Wow. That’s a long name, I probably should’ve  tried to make that shorter, huh? But each element of this dish is delicious and it would be horrible if I had to choose between them all!


This is going to be a new staple in your fall baking arsenal, I’m telling you right now. I was trying to recreate some of my favorite treats of my youth, but with a twist. It’s two soft, tender oatmeal cookies, nestled in cream cheese buttercream with a scoop of baked apples in the center. One bite of these cookies and it’s like every fall craving you’ve ever had. It’s simply divine.



The oatmeal cookies here are a little softer than a typical variety. I didn’t want the hard texture of the cookies to squish the filling inside out when you take a bite. So I upped my molasses content of my usual oatmeal cookie recipe and added a little more brown sugar too so give it that gooey texture. That way when you bite into the cookie you get equal portions of the cookie, apple filling and cream cheese icing without ruining the whole sandwich, or worse- spilling the cookie and getting it all over you. Because with a heavenly sandwich like this, it would be a shame to waste it, don’t you think?



Enjoy these cookie sandwiches, they would be great at a Halloween party or thanksgiving dessert. You can make the cookies, filling and icing several days ahead of time and just assemble them the day you want to serve, making it a great make-ahead meal to allow you time to enjoy the holiday you know, on the day of the holiday. They’re reminiscent of childhood for most of us, but with an added level of flavor and texture for us adults with the baked apples in there. The best of both worlds, I can’t wait for you to try these!




Oatmeal Whoopie Pies with Baked Apples and Cream Cheese Buttercream


Oatmeal Cookies:

1 C brown sugar

1 C white granulated sugar

1 C. Unsalted butter, at room temperature

2 eggs, at room temperature

1 tsp vanilla

½ tsp salt

1/3 C. Molasses (I used blackstrap, but any will work)

1 tsp baking soda

2 C. Flour

2 C. Old fashioned oats

1 tsp cinnamon


  1. Preheat oven to 350 degrees.

  2. In the bowl of stand mixer fitted with the paddle attachment, cream together the brown sugar butter, and white granulated sugar until pale and combined

  3. Add in the two eggs, vanilla and molasses-whisk thoroughly

  4. In a separate bowl, combine the dry ingredients: flour, salt, baking soda, cinnamon. Whisk to combine.

  5. Slowly add dry into wet until incorporated. Then add in oats.

  6. Scoop into whoopie pie pans or on a cookie sheet lined with parchment paper

  7. Bake at 350 for 13-15 minutes.

  8. Remove from oven and let cool completely before moving. Cookies WILL be soft, be careful handling them too much!


Cream Cheese Filling:

2 - 8 oz blocks of cream cheese, softened

1 tbsp vanilla extract

½ tsp butternut extract (I get mine from King Arthur flour, but you can use more vanilla if desired!)

5-6 cups confectioners sugar


  1. In the bowl of a stand mixer fitted with paddle attachment, whip the cream cheese and extract on low speed for 2-3 minutes until fully incorporated and smooth.

  2. Slowly add in the confectioners sugar a cup or two at a time on low until fully mixed in and at a stiff consistency

  • You can refrigerate this in a sealed plastic storage container until ready to use for 2-3 days, as long as it stays cold and is covered.


Baked apple filling:

4-5 empire apples,peeled and diced

½ C. Brown sugar

2 tsp All-Purpose Flour

1 tsp cinnamon

1/8 tsp nutmeg, freshly grated

1/8 tsp salt


  1. Place all ingredients into a large mixing bowl and toss to combine well, until no dry sugar remains on bottom of the bowl

  2. In a large sauté pan, pour apple mixture in and cook on medium heat for 5-7 minutes, stirring occasionally until apples are soft.

  3. Remove from heat and allow to cool to room temperature.


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