Preheat the oven to 400 degrees Fahrenheit and place cubed butternut squash on a foiled lined baking sheet.
Season and Cook Butternut Squash: Toss squash with olive oil, maple syrup, cinnamon, herbs and salt and pepper and arrange in a single layer. Roast the squash for 40-45 minutes until fork tender.
Puree Butternut Squash. Once done, save some of the roasted squash for garnish and puree the rest in a blender until smooth and set aside.
Saute Aromatics. Heat a wide dutch oven over medium heat and drizzle with olive oil and add butter. Once melted, saute chopped shallot for 3-4 minutes until just softened and add garlic and saute for another minute.
Stir in Arborio Rice. Stir in the arborio rice, making sure all of the the grains are coated with the olive oil and butter.
Pour in White Wine. stir the wine into the rice for 1-2 minutes so the alcohol cooks off and reduces.
Add the Stock. Steep the saffron in the vegetable stock. Ladle in 1-2 cups of stock, while continually stirring until the risotto is mostly cooked through, about 20-25 minutes.
Add the Pureed Squash. Stir in pureed squash with another ladle of stock and continue cooking for another 10 minutes until rice is tender and creamy.
Stir in Parmesan and Garnish: Stir in the grated Parmesan cheese and taste for seasoning. Ladle risotto into shallow bowls and top with cubed butternut squash fried sage leaves.