Preheat oven to 400 degrees F. Line a baking sheet with a silicone mat or foil. Coat bacon strips in brown sugar on both sides and lay flat on the baking sheet.
Bake for 15 to 20 minutes, or until the bacon is crispy. Remove from the oven and transfer to a pate that's been sprayed with non-stick cooking spray to let the candied bacon set up. Once cooled, finely chop the bacon.
While the bacon cooks, Place heavy cream in a large mixing bowl and beat on high speed until stiff peaks form. Set aside.
Peel and pit the peaches. Cut 4 peaches into chunks and place in a food processor or blender. Dice the 5th peach and set it aside. Add the sweetened condensed milk to the peaches and puree until smooth. (Use a rubber spatula to stir things around as needed.)
Add the peach mixture to the whipped cream and fold together until combined. Add the bourbon and 2/3 of the bacon to the ice cream base and stir to incorporate.
Pour the ice cream base into a 1/5 quart loaf pan. (There may be a little more base than can fit, it's happened to me before.) Sprinkle the reserved diced peach and remaining bacon on top of the ice cream base.