In a blender, combine 4 cups of vanilla ice cream, 1 cup of whole milk, 1 teaspoon of vanilla extract, and 1 teaspoon of black gel food coloring. Blend on medium speed for about 30 seconds until the mixture is smooth and creamy.

Taste the milkshake, and if you'd like it thicker, slowly add another scoop of vanilla ice cream and blend again for 15 seconds. Alternatively, if it's too thick, pour in a splash of milk until you reach your desired consistency.

While adjusting the consistency, prepare your serving glasses by chilling them in the freezer for about 10 minutes.

Carefully pour the blended mixture into your chilled glasses, filling them about three-quarters full. Top each milkshake with a generous swirl of whipped cream.

Sprinkle a handful of black and orange sprinkles onto the whipped cream. Layer on some crushed chocolate cookies and add your favorite Halloween-themed candy.

Insert black straws or spoons into each glass for easy sipping and serve immediately.