In a large bowl, whisk the cold milk and cheesecake pudding mix until a thick pudding forms. Add the condensed milk and vanilla, then mix until fully combined.
2 1/2 cups cold whole milk, 3.4 oz instant cheesecake pudding , 1 package, 1/2 cup condensed milk, 2 tsp vanilla bean paste, or vanilla extract
Cover and chill in the fridge for 10 minutes. (This helps the pudding fully set and thicken.)
Meanwhile, add the heavy cream to a deep bowl and mix on high until light and fluffy with stiff peaks. (It should be like whipped cream.)
2 cups heavy cream
Remove the cheesecake pudding from the fridge and, with a spatula, fold the whipped cream in the pudding until everything is fully combined.
Cover the bottom of the casserole dish with a layer of the pudding mix (about one-third of the pudding), spreading it evenly. (You can use a large or small casserole dish or any serving dish.)
Add a layer of broken graham crackers over the pudding mix, covering the entire dish. Top with a mixture of fresh fruit.
Add half of the remaining cheesecake pudding mix on top, spreading it into an even layer.
Repeat with another layer of graham crackers and fresh fruit.
Finish by spreading the rest of the pudding mix evenly over the dish, fully covering the wafers and fruit.
Cover the berry cheesecake pudding with plastic wrap and chill in the fridge for at least 6 hours or overnight.
Right before serving, top the cheesecake pudding with crushed graham crackers and fresh fruit.
Serve and enjoy!