In a blender, combine 4 large scoops of vanilla ice cream, 1 cup of milk, 1 teaspoon of vanilla extract, and 1 teaspoon of black gel food coloring. Blend on high speed for about 30-45 seconds until the mixture is smooth and creamy.

Taste your milkshake to see if you need to modify its texture. If you prefer a thicker shake, add an additional scoop of ice cream and blend for another 10-15 seconds. For a thinner milkshake, gradually pour in more milk, blending briefly until the consistency is to your liking.

While the milkshake is blending, take your tall glasses and place them in the freezer for about 10 minutes.

Carefully pour the blended black Halloween milkshake into the chilled glasses, filling each one about three-quarters full. Top with whipped cream.

Sprinkle a mix of black and orange sprinkles over the whipped cream. Add crushed chocolate cookies and finish with Halloween-themed candy.

Insert black straws or spoons into each milkshake for a fun presentation.