Bring apple cider to boil in a small saucepan over medium to medium high heat. Simmer it until it has reduced to 1/3 cup. Allow to cool completely before adding to cookies.
Preheat oven to 350°F, and line cookie sheet with parchment paper.
Cream butter and sugars in a large bowl until light and fluffy. Add in eggs and vanilla and mix. Add in reduced cider slowly and mix until combined.
In a separate bowl, combine flour, apple pie spice, baking soda, baking powder and salt. Alternate adding the buttermilk and the flour mixture into the butter mixture until everything is combined. Fold in apples until evenly distributed through the batter.
Using a 2 tablespoon cookie scoop, scoop batter onto prepared sheet. Bake for 11-13 minutes or until cookies are just set in the middle.
Cream butter and vanilla in a large bowl. Add 1/4 cup caramel and mix. Add in sugar and mix until combined. Add in whipping cream and whip about 3 minutes or until light and fluffy.
Once cookies are cooled, pipe caramel buttercream on top. Use extra caramel to drizzle across cookie.
Add 1/2-3/4 a teaspoon of apple butter to the center of each cookie on top of the icing. Garnish with a dried apple slice/chip.