In a blender, combine all ice cream, maple syrup, bourbon and milk. Blend until smooth.
Divide between two glasses. Top with whipped cream and a drizzle of more maple syrup. Serve with a straw.
Notes
Too much whiskey will make the milkshake too thin, so resist the urge to add more. Start with less and add gradually until you reach your desired flavor.A rich, creamy vanilla ice cream works best, as it blends smoothly and pairs perfectly with the maple and bourbon.