Preheat oven to 325 degrees. Prepare a deep baking dish (10x10) with olive oil; set aside.
Whisk eggs in a large bowl until well blended. Add bread cubes and toss until fully coated. Set aside.
Add ground sausage to a large skillet and cook over medium high heat until brown. Turn heat down and add chopped apple, onion, sage, and rosemary; season with salt and pepper. Cook, stirring, for 2-3 minutes or until fragrant.
Transfer sausage mixture to the bowl with the bread.
Combine milk, pumpkin puree and spices, then gently and slowly pour the milk and fold into the bread and sausage so that the bread maintains its shape. Transfer bread mixture to prepared baking dish.
Bake until golden and bubbly, about 1 hour and 10 minutes. Remove from oven and let stand 30 minutes before serving.
For my sweet little ones I added maple syrup and a dust of cinnamon with fresh sliced apples on the side. Garnish with more fresh herbs, if desired.
Enjoy a gourmet breakfast or brunch that you can make the night before!