Make the simple syrup by combining equal parts granulated sugar and water in a small saucepan. Place on medium heat, stirring occasionally for a about 5-7 minutes or until sugar has completely dissolved. Remove from heat and cool. I make this in big batches to keep in the refrigerator but for this recipe you can do about 1/4 cup sugar and 1/4 cup water and you'll have plenty.
Fill a cocktail shaker or mixing glass with ice cubes. Add bourbon, simple syrup, and bitters, and gently stir the cocktail using a bar spoon.
Place a large ice cube in each drinking glass and pour the cocktail over top (leaving the ice in the shaker). Make sure your glass isn't too full that the smoker touches the ice or liquid. You need a little space for the smoke.
Take a wide strip of orange peel and run the peel around the rim of each glass. You can place the orange peel directly into the drinks or garnish the rim with a fancy twist.
Before you garnish though, it's time to smoke! Follow the instructions on your cocktail smoker. If you have the SmokeTop: Add just a few wood chips into the top of the smoker. Place smoker directly on top of glass. Direct the torch lighter straight down the chimney. Smoke for 2-3 seconds. Remove top.
Garnish with a cherry or two and orange peel, and enjoy!