Slice the pound cake into 1 inch cubes.
Add the 4 cups of cold milk to a large (4-5 quarts) mixing bowl.
Sprinkle the 2 packages of instant vanilla pudding mix over the cold milk. Use either a whisk, or a handheld mixer on low speed, to mix the pudding for about 1 ½ – 2 minutes until the pudding begins to thicken (about the consistency of yogurt)
In a trifle bowl (3.25 quart -or- 104 ounce) create a single layer of 1-inch cake cubes at the bottom. (Be sure the cake cubes are uniform in size and tightly fitted to form a sturdy base for your trifle)
Spoon ⅓ of the pudding on top of the layer of pound cake. Use a spoon or an offset spatula to smooth the pudding evenly over the pound cake cubes.
Place a single layer of sliced peaches against the glass. Then lay a layer of peaches flat over the pudding. If some of the sliced peaches are a bit too thick, carefully use a kitchen knife to slice the peaches to appear more uniform in size. Reserve 4-6 peach slices for garnish. Repeat the layers. (You will end up with 3 layers of pound cake, 3 layers of pudding and 2 layers of peaches)
After you have smoothed the 3rd layer of pudding, top the pudding with the 8 ounce container of thawed whipped topping. Use a silicone spatula or an offset spatula to smooth the whipped topping to the edges of the trifle bowl.
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