In a blender, combine the vanilla ice cream, milk, peppermint extract, crushed peppermint candies (roughly crushed if using a high-speed blender), chocolate chips, and red food coloring (if using).
Blend the mixture until it's smooth and all the ingredients are well combined. You can adjust the milk or ice cream to achieve your desired milkshake consistency.
Taste the milkshake and adjust the amount of peppermint extract and crushed candies to your liking. Some people prefer a stronger peppermint flavor, while others like it milder.
Pour the milkshakes into your serving glasses, top them with whipped cream and a maraschino cherry and enjoy.