Place all the ingredients except whipped cream, 2 tablespoons of chocolate syrup, crushed Oreos, and caramel syrup in a blender and mix until smooth and creamy.
Drizzle caramel syrup on the walls of a tall glass and serve the frappuccino in the glass.
Top the frappuccino with whipped cream, drizzle the remaining chocolate syrup on top, sprinkle the crushed cookies, and enjoy.