Preheat oven to 400 degrees and cover a large rimmed baking sheet with aluminum foil.
Take a date and open it at the seam. Double check for pits. Stuff the date with about half a teaspoon of blue cheese (or more depending on the size of the date). Close the stuffed date at the seam to seal. Repeat process with all dates.
Place the dates, seam side down, in the middle of a piece of bacon and wrap the sides of the bacon around the dates. Carefully, poke a toothpick through the sides of each wrapped stuffed date.
Dip each wrapped stuffed date in brown sugar and place on the prepared baking sheet. Bake the dates seam side up with the overlapped bacon on the bottom. Bake for 15 to 20 minutes, then broil on LOW for 1 to 2 minutes until bacon is crisp.
Notes
Helpful Tip:Serve Devils on Horseback immediately, or at least while warm. This appetizer does not reheat well as the bacon will never be as crispy as the day they are first baked.