Place the Oreo cookies into a food processor and pulse until uniformly ground. Alternatively, you can place them into an airtight plastic bag and roll with a rolling pin. Place 2 tablespoons of the Oreo crumbs in a shallow dish or plate. Set the rest aside.
Using a butter knife, spread the frosting 1-2 inches down on two malt glasses. Roll the frosting in the Oreo crumbs. Set aside.
In a blender, pulse together the ice cream and milk until smooth. Add the Oreo crumbs and pulse to blend, but leave bits and pieces of the cookies.
Pour into the prepared malt glasses.
Top with whipped cream and maraschino cherry.
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Notes
Try mixing up the flavor by using different flavors of Oreos!