Spray baking sheet with cooking spray and set aside. Heat oven to 400 degrees.

Slice each squash length-wise pole to pole. Scrape seeds from each half and discard seeds. Drizzle 1 Tbsp oil over squash and season to taste with salt and pepper then place each half cut side down on baking sheet. Wrap garlic in foil and place on baking sheet. Place in oven and roast 1 hour or until softened and beginning to collapse. Remove from oven and set aside to cool.

When cool enough to handle, scrape flesh from squash and add to a large bowl along with the garlic cloves.

Place a Dutch oven or soup pot over medium high heat then add diced bacon. Sauté until crispy about 5 minutes then remove from pan and set aside on paper toweling to drain. Spoon out extra fat leaving only about 1 Tbsp in pot. Return to heat. Add onion and cook 3 minutes until onion is translucent. Add broth a little at a time scraping up any brown bits on bottom of pot. Add squash, garlic, ginger, sage, cayenne, and allspice. Bring to a boil, then simmer 5 minutes.

Puree soup by using an immersion blender or by pureeing in blender in small batches. If using blender do not fill more than half way. The hot soup can blow the lid off if you put too much in! Return soup to pot.

Stir in cream, Worcestershire sauce, and vinegar and bring back to a simmer. Add salt and pepper to taste and serve with your choice of shredded Parmesan, bacon bits, pumpkin seeds and chopped parsley as garnish.