01 - Place vanilla ice cream, whole milk, mint extract, sugar if using, and food coloring if desired into blender canister. Secure lid tightly.
02 - Blend on high speed for 45-60 seconds until mixture becomes completely smooth and creamy with no ice cream chunks remaining.
03 - Taste milkshake and add additional sugar or mint extract in small increments if needed to achieve desired sweetness and mint intensity. Blend briefly to incorporate.
04 - Pour blended milkshake evenly into two chilled glasses, filling each to about 1 inch below rim to allow room for toppings.
05 - Top each serving with a generous swirl of whipped cream. Place one maraschino cherry on whipped cream of each glass. Serve immediately while cold.