Drizzle approximately 1-2 tablespoons of chocolate syrup on the inside of each glass. Start at the top, near the rim, and allow the chocolate syrup to drizzle down the sides to the bottom. Transfer your glasses to the freezer to chill.
To the bowl of a blender add the stemmed Maraschino Cherries (add more or less to suit your own personal taste and preference), cherry juice, freshly brewed coffee or espresso, and bourbon. Pulse until the cherries are chopped into small bits.
Add the ice cream. Blend until smooth. Add the milk, if desired.
Take your prepared glasses from the freezer and fill with your prepared Cherry Bourbon Milkshake. Garnish to whipped cream, chopped up chocolate chips, cherry juice, and Royal Harvest Bordeaux Maraschino Cherries, if desired.