Preheat oven to 400 degrees. Slice squash lengthwise and rub with olive oil or ghee. Place face down on baking sheet and roast for 45-50 minutes.
Heat 3 tablespoons ghee or oil over medium heat in a Dutch oven or large pot. Add garlic, onion, carrots, celery, bay leaf, thyme, and baking soda. Season with a teaspoon of salt. Cook, stirring occasionaly until vegetables just begin to brown, about 10 minutes.
Remove flesh from squash and add to pot along with apples, cinnamon, and water. Bring to a boil, reduce heat, cover and simmer for 15 minutes.
Remove bay leaf and process soup in batches in a high-speed blender. Keep about 1 cup of soup in blender and add Dandy Blend, honey, and coconut milk. Blend until foamy. Add to soup.
Stir in 2 tablespoons of truffle oil. Season with salt and pepper. Serve with a drizzle of truffle oil.