Preheat the oven to 400 degrees F. Spray a cooling rack with non-stick cooking spray. Place the cooling rack over a baking sheet lined with aluminum foil. (This is for easy cleanup.)
Coat both sides of the bacon with brown sugar, then place on the prepared cooling rack. Bake for 15-20 minutes, or until the bacon looks caramelized and crispy. Be careful that they don't burn! Cool the bacon on parchment paper.
Whip the cream with a whisk or hand mixer until it forms sturdy peaks. Make sure you whip only until peaks form. Overwhipping will turn your ice cream into butter!
Whisk in the sweetened condensed milk, vanilla and maple extracts until well combined. Then pour into a large casserole or baking dish. A loaf ban also works well.
Chop the candied bacon and sprinkle over the ice cream. Freeze for 6+ hours.
Weave bacon onto wooden skewers; arrange on a foil-lined baking sheet fitted with a wire rack.
Bake, turning once, for 20 to 25 minutes or until crisp.
Transfer to a paper towel-lined plate; let cool completely.
In microwavable bowl, combine chocolate and shortening; microwave on high, in 30-second intervals, stirring between each interval until smooth. Stir in chili powder, cinnamon and cayenne until well combined.
Position bacon skewers over melted chocolate mixture; drizzle chocolate mixture over bacon, allowing excess to drip back into the bowl.
Transfer to parchment paper-lined tray. Sprinkle with pepitas. Let stand until set.
If desired, you can garnish with a variety of items, such as chopped dried apricots, candied ginger, toasted coconut, chopped pecans or crushed peanuts.