Mix cream cheese, brown sugar, and vanilla extract in a bowl until smooth. Refrigerate until cold, about 30 minutes.
In a separate bowl, lightly mix together the chopped strawberries, pineapple, grapes, and the blueberries.
Scoop about 3 tablespoons of the cream cheese mixture into the bottom of each plastic cup to make a half-inch thick layer. Spoon enough mixed fruit on top of the cream cheese to make a 2-inch layer, about 1/3 cup. Top the fruit with a teaspoon or two of crumbled sugar cookies.
Garnish each trifle with a kiwi slice. Refrigerate until serving time.