Preheat the oven to 350 degrees F and line a sheet pan (10x15") with foil or parchment paper.
Remove bacon from package and cut into thirds -- you want each piece to be 3-4 inches long (you want it to wrap a little more than once around, since the bacon will shrink as it cooks).
Wrap one piece of bacon around every smokie, secure with a toothpick, and place on the pan. Repeat until all smokies are used (extra bacon? Throw it in the freezer!).
Combine brown sugar and chili powder if using. Sprinkle evenly over smokies in pan.
Bake for 35-45 minutes, until bacon is crispy. Remove from the oven and let cool for at least 10 minutes before serving.