Reserve 5 Oreos for garnish and crush the remaining Oreos into bite-sized pieces; set aside.
In a large bowl beat the cream cheese until smooth. Slowly add sugar and 1/4 cup of milk. Beat until creamy, then stir in 2 cups of whipped topping; set aside. Reserve remaining whipped topping for later use.
In a large bowl, whisk together pudding mix and remaining 4 cups of milk for 2 minutes.
To assemble:
Layer 1/3 of Oreos into a 3-quart trifle bowl. Top with 1/3 of pudding followed by 1/2 of the cream cheese mixture.
Repeat with 1/3 of Oreos, 1/3 of pudding and remaining 1/2 of cream cheese mixture
Finish with last 1/3 of Oreos and last 1/3 of pudding. Garnish with remaining 1 cup of whipped topping and reserved Oreo cookies.