Preheat the oven to 400 degrees F (200 degrees C). Line a baking sheet with parchment paper.
Pat pickles dry with a paper towel. Cut cream cheese into 8 strips. Place 1 strip onto each pickle, and wrap with a strip of bacon, securing ends with toothpicks if necessary. Place pickles on the baking sheet.
Bake in the preheated oven until bacon is browned, 12 to 15 minutes. Let cool slightly, then serve with ranch dressing.