In a medium bowl, mix the vanilla pudding with half of the whipped topping until well combined.
In serving cups or bowls, layer the crushed chocolate sandwich cookies at the bottom.
Add a layer of the vanilla pudding mixture on top of the cookie layer.
Next, add a layer of diced strawberries followed by a layer of blueberries.
Repeat the layers until the cups are filled, finishing with a layer of whipped topping on top.
Drizzle chocolate syrup over the whipped topping for decoration.
Chill in the refrigerator for at least 30 minutes before serving to allow flavors to meld.