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Preheat oven to 400°F.
Line a rimmed baking sheet with aluminum foil.
Wrap each pickled watermelon rind piece with 1 bacon half; secure with a wooden pick.
Arrange wrapped pieces on prepared baking sheet spaced at least ½ inch apart.
Bake in preheated oven until bacon is mostly rendered and starting to brown, 20 to 25 minutes.
Flip each piece, and continue baking until bacon is browned and crisp on both sides, 5 to 10 minutes.
Carefully transfer pieces to a platter, letting excess drippings drip off onto baking sheet.
Discard drippings.
Serve immediately.