Preheat oven to 450 degrees and line a baking sheet with parchment paper.

Cook bacon until lightly cooked but still pliable, about 13 minutes, depending on thickness of bacon.

While bacon cooks, using a spoon, de-seed pickles. Blot each de-seeded pickle with a paper towel to remove any excess moisture then, using a knife, slice pickles in half.

Remove baking sheet of bacon from oven. Do not turn oven off. Transfer bacon to paper towel-lined plate to de-grease.

In a mixing bowl, combine cream cheese, dill, and pepper. Spoon and flatten mixture atop each pickle then wrap each pickle with bacon and secure bacon with a toothpick. Transfer bacon-wrapped pickles to baking sheet used to cook bacon then transfer baking sheet back to oven and bake until bacon is crispy, about 7 minutes.