Preheat oven to 400F. Slice squash in half, lengthwise. Use a spoon to scoop out seeds. Drizzle the flesh of each half of the squash with a bit of EVOO and season with a pinch each of salt and pepper. Place squash halves on a roasting tray, flesh side up, and roast 40-45 min or until fork tender.
While the squash roasts, chop the carrots, onion, leek and garlic. Then, preheat a large stockpot or Dutch oven over med heat. Add three tablespoons EVOO along with the carrots, onion, and leek. Season with a pinch of salt and sweat veggies until they are soft (approx. 12-15min).
Add garlic and cook an additional 60 seconds. Add paprika and cook 60 more.
Deglaze the pot with stock and bring everything to a steady simmer.
Remove squash from oven and carefully spoon out all of the flesh from each half - discard the skin. Add the roasted squash flesh to the soup and cook 5-10 minutes, stirring regularly.
Transfer soup to a high-powered blender (or use an immersion blender) and purée the soup until smooth and creamy. Return soup to pot and taste for seasoning. Adjust salt and pepper as required.
Ladle Roasted Squash Soup into individual serving bowls, season with an extra crack of black pepper and garnish with swirls of EVOO and maple syrup.