Fill a martini glass with ice and water. Set aside to chill.
Fill a cocktail shaker with ice. Pour in the bourbon, sweet vermouth, and bitters. Cover and shake vigorously for 20-30 seconds until chilled (or stir with a bar spoon).
Dump the ice water out of the martini glass. Strain the cocktail into the chilled glass and garnish with a few cherries on a cocktail pick. Serve immediately.