Preheat the oven to 400˚F.
In a large roasting pan, toss the butternut squash pieces with 3 tablespoons of the olive oil, the fresh thyme leaves, and the salt and pepper. Roast in the oven for approximately 35- 40 minutes, tossing once halfway through, until the squash is fork tender and lightly golden. Remove from the oven and set aside.
In a medium saucepan, warm the chicken stock over low heat. In a separate large stockpot, heat the remaining 2 tablespoons olive oil over a medium-high heat. Add the shallots and garlic and sauté until translucent and softened, about 5 – 7 minutes. Add the rice and cook for about 2 minutes, stirring to coat it in the olive oil. Add the white wine and reduce the heat to medium. Simmer, stirring, until most of the liquid has been absorbed. Add 2 ladles of the warm chicken stock and gently simmer, stirring frequently, until most of the liquid has been absorbed. Continue adding stock, 2 ladles at a time, waiting until most of the liquid has been absorbed before adding more, until you have used all the stock and the rice is cooked through. The process should take about 25 minutes total. If you find the rice is not cooked after adding all of the chicken stock, add 1 – 2 ladles of water and simmer until the rice has finished cooking.
Stir in the parmesan cheese and add the roasted squash. Serve immediately with crispy bacon on top, if desired, and additional cheese on the side for sprinkling.
If you are not worried about keeping this recipe strictly vegetarian, you can substitute chicken stock for the vegetable stock.