Preheat oven and boil a pot of water. Remove seeds and insides of the pumpkin. Pierce the inside and outside of the pumpkin.
Add bourbon to the bottom. Rub the inside with brown sugar. Place in a cast iron pan. Bake for 35 to 40 minutes.
Dice potatoes, add to water, and cook. Drain. Melt butter. Sauté onions. Add beef and seasonings. Add potatoes and mash in.
Scoop stuffing into the roasted pumpkin. Replace the top, return to a 375F oven, and bake for 20 minutes.