Preheat the oven to 400°F and roast the pumpkin for 35 to 40 minutes, until the inside becomes more tender.
In a large bowl, mix together the milk, beaten eggs, butter, cinnamon, maple syrup and vanilla extract. Immerse the challah slices in the bowl one by one and lay them flat on a plate. Heat up one tablespoon of butter in a large pan. Fry the bread for about 2 minutes on each side.
Slice up the french toast into small bites and toss them inside the pumpkin. Sprinkle some cinnamon on top.
To serve: scoop out some of the pumpkin along with the challah bites and serve with fresh fruits. Drizzle some maple syrup on top.