In a roasting pan, combine the prepared butternut squash with the peeled and chopped pear. Stir in 2 tablespoons olive oil, salt, pepper and add cinnamon stick. Roast for 35-40 minutes at 400° till soft and slightly browned. Set aside.
Bring a Dutch oven up to medium-high heat on the stovetop, combine shallots, celery, garlic, ginger and remaining olive oil and sauté for 10 minutes stirring constantly. When finished, add roasted squash, pears and vegetable broth.
Reduce heat under Dutch oven to medium-low and simmer uncovered for 25 minutes.
Let cool slightly then put the soup in a blender (in batches) and purée until almost smooth. Add the coconut milk and maple syrup as you purée.