Using a paring knife, cut off the bottom of the orange and use that as the base. Carefully cut off a piece of peel by moving the knife away from yourself in a downward direction. Try to cut shallowly to minimize the amount of white pith.

In a cocktail shaker, add the apple cider, bourbon and a handful of ice. Put on the top and shake vigorously for about 15 seconds.

If desired, on a small plate, mix together the cinnamon and sugar. Run an orange slice around the rim of the glass and dip in the cinnamon-sugar mixture. Fill the glass with ice and pour in the chilled apple cider and bourbon. Pour a splash of ginger ale on top and gently stir. Twist the orange peel over your drink to release the oils and drop in the glass with an apple slice if desired. Enjoy!