Preheat the oven to 325°F. Place the ham cut sides down in a roasting pan. Cover the ham with aluminum foil. Bake for about 1 hour and 30 minutes or until a meat thermometer inserted in the thickest portion registers 130°F. (Note: The ham will take about 12 to 15 minutes per pound to reach the finished temperature of 140°F.)
Meanwhile, combine the cherries, cherry syrup, and orange juice in a food processor or blender and process until smooth.
Transfer the cherry mixture to a medium saucepan. Add the brown sugar, bourbon, and bitters and simmer until syrupy, about 5 minutes. The glaze will thicken as it cools.
Remove the ham from the oven and remove the aluminum foil. Pour all but ½ cup of the glaze over the ham. Return to the oven and bake, uncovered, for 20 minutes or until the ham reaches 140°F.
Remove from the oven, transfer to a serving platter, and brush with the reserved glaze. Garnish with oranges, cherries, and fresh bay leaves, if desired.