1. Prepare the glass by making the cinnamon sugar rim. Mix coarse sugar and ground cinnamon in a small bowl. Wet the rim of the serving glass with an orange wedge or a bit of lemon juice, then dip the rim into the mixture. Set aside.
2. Muddle fresh pineapple. In a cocktail shaker, add 1 cup of fresh pineapple chunks. Use a muddler or the back of a wooden spoon to gently crush the pineapple until it releases its juices.
3. Add liquids to the shaker. Pour in 2 ounces of bourbon, 1 ounce of freshly squeezed lemon juice, and 1 ounce of simple syrup or brown sugar syrup. Add a pinch of ground cinnamon for a warm, spiced flavor.
4. Add ice and shake. Fill the cocktail shaker with ice cubes, securely close the lid, and shake vigorously for about 15 seconds to blend and chill the ingredients.
5. Strain the mixture into the prepared glass. Use a fine mesh strainer if you prefer a smoother drink with fewer pineapple fibers, ensuring you don’t disturb the cinnamon sugar rim.
6. Add garnish. Enhance the presentation with a garnish like a cinnamon stick, a fresh mint sprig, or a pineapple wedge for extra visual appeal.
7. Serve immediately and enjoy the rich flavors of the Cinnamon Sugar Pineapple Bourbon Smash as your perfect fall-inspired cocktail.