In a mixing bowl whisk together eggs and ¼ cup brown sugar. Whisk in milk and vanilla extract.
Place cubed bread in a greased 9x13 glass or ceramic baking dish. Pour milk mixture over the bread and stir to combine. Allow to sit 15-20 minutes. Preheat the oven to 350 degrees.
In a large saucepan, melt 2 tablespoons butter. Add apples, cranberries, remaining ¼ cup brown sugar and orange juice; stir to combine. Bring to a simmer and allow to cook 4-5 minutes, until fruit just starts to soften. Stir in cinnamon and nutmeg.
Pour apple/cranberry mixture over the bread mixture and stir to combine. Bake 40 minutes.
In a small glass mixing bowl, melt remaining ½ tablespoon butter. Stir in granola to combine. Top bread mixture with granola mixture. Bake an additional 10-20 minutes, until top is puffed and light golden brown. Allow to slightly cool and serve with maple syrup.