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Slice bread into thick slices about an inch thick. 1 loaf Challah bread
Whisk milk, eggs, cinnamon, vanilla and sugar together in a medium bowl or shallow dish. 1 cup 2% milk, 8 large eggs, 1 tablespoon cinnamon, 1 teaspoon vanilla extract, 3 tablespoons granulated sugar
Dunk each piece of bread into mixture and turn the bread to coat. Allow the egg mixture soak into the bread slightly.
Lift bread slices out of the milk mixture and onto a hot waffle iron. Cook until golden brown. Remove and repeat with the remaining slices of bread.
Place cooked waffles on a wire rack if desired to keep them from getting soggy. Serve with melted butter and maple syrup.