Preheat oven to 375° and coat mini muffin pan with cisco or with a light spray of cooking spray.
Brown butter in a sauce pan over medium heat. Once butter is melted, stir constantly until butter turns light brown and starts to have a nutty aroma.
Combine browned butter with sugar and light brown sugar and beat on medium speed until well creamed together.
Add egg, vanilla and maple syrup. Mix into butter and sugar until egg is well beaten.
In a separate bowl, combine flour, baking soda and cream of tartar. Slowly add into batter and beat on medium low speed until well combined.
On a small plate, combine sugar and cinnamon and stir to combine. Measure out about two tablespoons of dough. Roll into a ball and then roll in cinnamon sugar mixture.
Place into a mini muffin pan. Bake at 375° for 10-14 minutes until they turn light brown.
Remove from oven and allow to set for 5-10 minutes. Use a tart shaper and gently press into the center of the cookie to form a cup.
Allow cookies to set for another 10 minutes before removing from muffin tin. Allow to cool completely.
For the Frosting
Allow butter to come to room temperature. Using a stand mixer, beat the butter for several minutes until light and fluffy.
Add powdered sugar and slowly increase speed from low to medium. Frosting will become thicker. Add heavy whipped cream and increase speed to medium high; beat for several minutes until light and fluffy.
Lastly, add maple syrup and cinnamon and beat until incorporated.
Fill cookie cups with frosting once cookies are cooled.