Make the Bacon: Preheat oven to 375 degrees F. Line a baking sheet with parchment paper, a silicone baking mat, or spray a baking sheet with non stick cooking spray and line with foil. Arrange bacon in a single layer on the baking sheet. Sprinkle generously with the brown sugar. Place in the upper third of the oven and bake until sugar is caramelized and bacon is brown and crispy, about 10 to 15 minutes. Remove from oven. Immediately remove bacon slices using a pair of tongs. Place them on a cutting board (not paper towels, they’ll stick!) to cool. Once cool, chop the bacon into bite size bits and set aside.
Make the Waffles: Preheat your waffle iron.
In a large bowl, whisk together the flour, baking powder, baking soda, salt and brown sugar. In a medium bowl, whisk together the eggs, oil, buttermilk and vanilla extract. Add the wet ingredients to the dry ingredients and fold with a rubber spatula. Once almost fully incorporated, add the bacon and stir. Mix only until most of the dry ingredients are moistened in the batter; like pancakes, it's good to have a lumpy batter.
Cook the waffles according to your waffle machine instructions.
Serve with butter and maple syrup. Leftover waffles can be stored in an airtight container in the refrigerator for up to 4 days, or wrapped in plastic wrap and placed in a ziploc freezer bag and stored in the freezer for up to 2 months. My favorite my to reheat them (whether fresh or frozen) is in a toaster oven.