In a large trifle dish or a glass bowl, layer half of the crumbled chocolate chip cookies evenly at the bottom.
Spoon half of the vanilla pudding over the cookie layer, spreading it gently to cover completely.
Add half of the whipped cream on top of the pudding layer, smoothing it out with a spatula.
Sprinkle half of the mini marshmallows over the whipped cream layer.
Drizzle half of the chocolate syrup over the marshmallows.
Add half of the sliced strawberries and blueberries on top of the chocolate syrup.
Repeat the layering process with the remaining ingredients, starting with the cookie crumbles and ending with the fresh fruit on top.
Chill the trifle in the refrigerator for at least 1 hour before serving to allow the flavors to meld.