Preheat to 350. Cut squash in half, drizzle with olive oil, season with salt and pepper. Put a shallot and a clove of garlic in each half. Roast until soft about an hour. Remove skin when cooled. In large Dutch oven heat olive oil and 2 TB butter over medium high. Saute minced shallots until starting to carmelize. Deglaze with 1/2 cup of stock, add squash, garlic, and whole shallots. Add remaining stock. Add herbs, Worcestershire, and cream. Blend with stick blender or put in blender. Add parmesan. Simmer to mix flavors. Season to taste. Serve with drizzle of cream on top and dash of cayenne pepper and chopped parsley. Garnish with crostini (chopped pistachios, butter, and parm, broil).