Preheat oven to 350 F. Line a large rimmed baking sheet with parchment paper. Put all the apples on the sheet and toss with maple syrup and olive oil to coat. Spread out into a single layer. Scatter in the cranberries and ginger and then sprinkle on the brown sugar.
Cover loosely with tin foil and bake for 20 minutes. Remove the tin foil and flip the apples. Bake for 15 more minutes or until tender and slightly browned.
While the apples are baking prepare your shallots. I used the same cast iron pan for the shallots and the cutlets to cut down on dish duty. Just saute the shallots in the oil over medium high until shallots are nice and brown and crispy in spots. Transfer them to a bowl and cover with tin foil to keep warm.