The braised bacon and the reduced braising liquid can be refrigerated, separately, up to one day. Let the bacon stand at room temperature one hour, and reheat glaze to warm before caramelizing the bacon.
Preheat oven to 325 degrees. Place bacon in an 8-inch square baking dish, and rub all over with pepper. Bring cider and maple syrup to a boil in a small saucepan, and pour over bacon. Cover with foil, and braise bacon in oven 55 minutes. Turn over bacon, cover, and braise 50 minutes more. Remove foil, and let bacon cool in liquid.
Remove bacon from braising liquid, and cut into 1/4-inch-thick slices. Transfer liquid to a small saucepan; bring to a boil, and cook until reduced to a glaze (you should have 1/3 cup).
Toss bacon in glaze to coat, and cook in a nonstick pan or preheated cast-iron skillet over medium heat, turning once, until deep brown and caramelized, 3 to 4 minutes total.