First, soak the wooden skewers in a large baking dish with one inch of water if using wooden skewers. Combine the brown sugar, maple syrup, bourbon, and ketchup in a small saucepan.
Bring the brown sugar bourbon glaze to a low simmer over low heat. Stir with a whisk for five minutes, just until the sugar has dissolved. Remove from the heat and set aside.
Preheat the oven to 350°F. Line a large rimmed baking sheet with tin foil or parchment paper and place an oven-proof wire rack on top. Once the skewers have soaked, pat them dry with a paper towel. Next, thread one strip of bacon onto each wooden skewer. Spread the folds of the bacon slices apart so they are not too close or overlapping in any one area. Lay each bacon skewer in a single layer on the wire rack.
Lightly brush the bourbon brown sugar glaze over the tops of each bacon skewer. Bake the glazed bacon skewers in the oven for ten minutes.
Next, remove the bourbon-candied bacon from the oven and carefully turn each bacon skewer over. Brush the brown sugar glaze mixture onto the other side of each skewer and bake for another ten minutes.
After ten minutes, remove the candied bacon from the oven and turn the bacon over again. Continue baking the bacon skewers until they have reached the desired crispiness, checking on them every five minutes. Note: The time it will take to cook your bacon will depend on the thickness. Remove caramalized bacon skewers from the oven, allow the bacon to cool for three minutes, then remove them from the wire rack.