Preheat the oven to 350°. In a large deep skillet, heat the oil over medium heat, add bacon and cook until rendered, about two minutes Season the drumsticks with salt and pepper, add them to the skillet and cook over moderate heat, turning, until browned all over, about eight minutes. Transfer the drumsticks to a platter.
Add the celery, carrot, onion and a pinch of each salt and pepper to the skillet and cook over moderate heat until the onion is translucent, about five minutes. Add the squash, white wine, cider, stock, bay leaves and thyme and bring to a boil. Pour the mixture into a large roasting pan. Add the drumsticks and cover tightly with foil. Braise the turkey in the oven for 45 minutes. Uncover and braise for 15 to 20 minutes longer, until an instant-read thermometer inserted in the thickest part of the thigh registers 160°. Carve the drumsticks and transfer the meat to a deep serving platter.