If using a cinnamon-sugar rim, dip the glass edge in caramel sauce and then in ground cinnamon.
Fill the cocktail shaker halfway with ice cubes.
Pour the whiskey, caramel syrup, apple cider, and lemon juice into the shaker.
Shake vigorously for 15-20 seconds until well chilled.
Fill the highball glass with fresh ice cubes.
Strain the mixture into the glass.
Garnish with fresh apple slices.
Notes
The drink works best with fresh, high-quality apple cider rather than apple juice.Store-bought caramel syrup is fine, but homemade adds extra richness to the drink.Choose a bourbon that's not too expensive but still smooth. Mid-range options like Buffalo Trace or Maker's Mark work great.The cocktail can be served hot - just warm the apple cider before mixing.For a less sweet version, reduce the caramel syrup to 1/2 oz.