Crush the 8 Oreo cookies in a sealed zip-lock bag with a rolling pin until you have a mix of fine crumbs and pea-sized pieces, about 30 seconds.

Blend the 2 cups vanilla ice cream, 3 tbsp whole milk, 2 tbsp heavy cream, 1/2 tsp peppermint extract, and 2 drops green food coloring on medium speed for about 20 seconds until thick and smooth.

Pour into 2 chilled glasses, fold the crushed Oreos through 3 or 4 times, garnish the surface with extra crumbles, and serve immediately.