Soak 32 toothpicks or small wooden skewers in water 30 minutes. Preheat oven to 350 degrees. Meanwhile, cook bacon in a large skillet over medium until some of fat is rendered but bacon is still pliable, about 5 minutes. Transfer to a paper towel-lined plate to drain.

Place cream cheese in a piping bag or a resealable plastic bag. Snip tip and pipe cheese into peppers to fill. Wrap each pepper with a piece of bacon; insert a toothpick all the way through each pepper, beginning where bacon overlaps.

Transfer stuffed peppers to a parchment-lined rimmed baking sheet, in a single layer, and bake until bacon is crisp, 12 to 14 minutes. Serve warm.