Gather all of your ingredients and gear for a smoother process.
In your blender, combine the 4 cups of vanilla ice cream and 1 cup of milk. Blend on medium speed until smooth and creamy.
Add in the ½ cup of crushed peppermint candy, ½ cup of semi-sweet chocolate chips, and a few drops of red gel food coloring. Blend again until well incorporated.
Taste your milkshake and adjust the peppermint or chocolate levels if desired.
Pour the milkshake into serving glasses, and top generously with whipped cream and a maraschino cherry.