Preheat oven to 300°. In a large sauté pan, brown the sausage, breaking it up into small pieces. Add apple, fennel, onion and butter and cook until onions are translucent. Add thyme, sage and rosemary. Remove from heat and let cool.
Combine eggs, Hood® Heavy Cream, Hood® Whole Milk, salt and pepper and whisk until smooth. Add cubed bread and let soak for 15 minutes. Add sausage mixture to bread and mix gently until combined.
Cut the top off the sugar pumpkin 2 inches from the top. Hollow out seeds, scraping the inside of the pumpkin so it is clean. Fill the pumpkin with the sausage mixture and cover with foil. Bake at 300° until pumpkin is soft when punctured and filling is hot throughout, about 45 min to 1 hour. Bake the pumpkin top separately alongside the pumpkin. Remove foil and continue baking the pumpkin until the top of the stuffing is golden brown, approximately 10 minutes.
Remove pumpkin from the oven and let stand for 15 minutes. Serve covered with the pumpkin top. When serving, be sure to scoop pumpkin flesh out with the stuffing.
If the pumpkin is out of season or there is extra stuffing, the stuffing can be cooked in the baking pan alone. Cook at 300° for 30-45 minutes or until set throughout and golden brown.