Tightly wrap one piece of bacon around one little sausage. Place seam down in a glass 13x9 dish. Repeat with remaining little smokies.
Sprinkle evenly with brown sugar. There should be a thin layer over all the little smokies. Cover and refrigerate for at least 1 hour.
Preheat oven to 350°F. Uncover little smokies and bake for 40-50 minutes. Bacon should be crispy and sugar deeply caramelized.
Video
Notes
Start with cutting the bacon into thirds. If you leave the strips any longer they will never crisp up. There may be a few pieces of bacon left over.
You can make this ahead and bake when you are ready!
As for the pan you use, this makes a big difference. I asked my mom how she did it and she said she uses a glass baking dish, not a foil-lined baking sheet. To clean up after, she fills the pan with hot tap water and lets it sit for a few minutes. The caramelized sugar dissolves away.
Letting them marinate makes all the difference in flavor.