Add the water and pudding mix to a bowl. Whisk until smooth. Add the sweetened condensed milk and whisk again until the mixture is completely smooth. Cover and transfer to the fridge for at least 4 hours, or overnight until it sets up.

About an hour before removing the pudding mixture from the fridge, begin preparing the remaining things. Preheat the oven to 350F. Add all of the cinnamon crumble ingredients to a bowl (flour, brown sugar, butter, cinnamon). Mix until well combined. The mixture should adhere together but shouldn't be sticky.

Transfer the mixture to a lined baking sheet and spread it out. Transfer to the oven for 10 minutes. After 10 minutes, remove from the oven and use a fork to break it into smaller pieces (I just drag the fork back and forth to break it up). Transfer it back to the oven for 5 more minutes and break it up with a fork again. Allow it to cool completely and you should have pieces of cinnamon crumble.

Add the heavy cream to a large bowl. Use a hand or stand mixer to whip the heavy cream until soft peaks form.

Remove the pudding mixture from the fridge. Add 1/3 of the whipped cream to the pudding mixture and gently mix until combined. Add the remaining whipped cream and gently mix until smooth and combined.

Slice the peaches into small bite sized pieces (you can peel them or leave the skin on -- I like to leave the skin on).

In a trifle bowl, layer the pudding, vanilla wafers, fresh peaches, and cinnamon crumble. Continue until you use all the pudding mixture! Refrigerate for at least another 30 minutes before serving. Enjoy!