Apple Whoopie Pies with Cinnamon Caramel Cream Cheese Filling

It seems like when fall weather first hits, my mind automatically goes to all pumpkin, all the time. My pumpkin love runs deep and true. But with all my pumpkin adoration, I tend to forget about that other delightful seasonal fall ingredient: the apple. I couldn’t let autumn pass without baking with apples at least once, and right about the time I vowed to make something apple-icious, Stephanie serendipitously posted these whoopie pies. Done, and done.

I learned a lesson while making these. I knew the filling was going to be amazing (cinnamon cream cheese frosting, I mean, come ON), but I decided I wanted to make it even better and add some caramel. Sounds delicious, right? I had half a bag of caramels in the cupboard from when I made these snickerdoodles, so I thought that would be the perfect thing to use. But, um, do you know what happens to caramel after you melt it? It starts to harden up IMMEDIATELY. When I tried to add it to the frosting, it got all clumpy – not to mention the mess I made of my stand mixer. There were bits of caramel everywhere. In hindsight, I should have tempered the caramel with the frosting. Or I should have just made my own caramel.

My second attempt at the frosting was much better (good thing I always keep myself supplied with cream cheese and powdered sugar!). I used caramel ice cream topping instead. I don’t know what they add to it to keep it soft (nor do I really want to know), but it worked perfectly. The filling was AMAZING – nutty and sweet from the caramel, and spicy from the cinnamon. It was such a perfect flavor combination.

The apple whoopie pies themselves were pretty delicious, too. They had a nice amount of spice, and I loved the texture that the bits of apple added to them. Joe and my boys loved them. Andrew kept calling them “apple pie whoopie cookies,” which was pretty cute. :)

Apple Whoopie Pies with Cinnamon Caramel Cream Cheese Filling
adapted from Macaroni and Cheesecake

For the whoopie pies:

1/2 cup butter, softened
1 1/4 cups brown sugar, packed
1 teaspoon baking soda
1 teaspoon apple pie spice
1/4 teaspoon salt
1 egg
1/4 cup applesauce
1/4 cup milk
2 1/2 cups all purpose flour
1 large Granny Smith apple, peeled and grated

For the frosting:

1/2 cup butter
1 8-ounce package cream cheese
3/4 cup caramel ice cream topping
1 teaspoon vanilla
1/2 teaspoon cinnamon
5 cups confectioners’ sugar

1. Preheat oven to 350 degrees. Cover baking sheets with parchment paper; set aside.

2. In the bowl of a stand mixer fitted with the paddle attachment, add butter and beat on medium speed until creamy (about 30 seconds). Add in brown sugar, baking soda, apple pie spice and salt. Beat on medium speed until well incorporated. Add egg and beat until combined. Add in applesauce and milk and mix on low speed until fully incorporated. Add in flour a little at a time and mix until combined. Add apple and fold into mixture with spatula.

3. Using a small cookie scoop or tablespoon, scoop dough onto prepared baking sheets approximately 2 inches apart. Bake for 10 to 12 minutes until tops are lightly browned. Let stand a couple minutes on cookie sheets to set and then transfer to cooling rack to cool completely.

4. For the frosting, in the bowl of a stand mixer, beat together butter and cream cheese until creamy. Add caramel and mix until combined. Add in confectioner’s sugar, vanilla and cinnamon. Beat until light and fluffy and a spreadable consistency.

5. Add frosting to the flat side of one cookie, and top with another cookie. Chill before serving. Makes 18 whoopie pies.