Preheat the oven to 425°F. Cut the squash in half and set one half aside for another use.
Cut off the top of the garlic and wrap tightly in foil.
Place the squash on a parchment lined baking sheet. Add the garlic and roast for 20-25 minutes or until the squash is soft.
Add the cooked squash (it should yield about 2 cups) and garlic to a blender. Add the vegetable stock, 2 cups of water and 1 tbsp of kosher salt. Blend until smooth. It will be very watery, think of it as a butternut-broth.
Add this butternut broth to a pot and put it on medium heat. Let it come to a simmer and then lower the heat so that it is kept warm but not boiling.
In a large, high-sided sauté pan, add the 6 tbsp of olive oil and bring it to medium heat. Add the onion, season with salt and stir. Cook the onion for 6-8 minutes or until soft.
Add a generous splash of water to the pan to help the onion cook until it is transluscent. The water should evaporate in about 5 minutes, and the onion should be soft and almost "melted." If the onion still has some bite to it, add another splash of water and repeat.
Add in the rice and stir to coat in the oil and onion. This is pre-cooking the rice, so that when you begin the risotto process, the rice will cook evenly in the broth. Cook on medium heat for about 5-6 minutes, or until the outside edges of the rice are clear, and the rice makes a clattering sound when it hits the edges of the pan.
Add in the wine, stir to combine, and let the wine reduce. Season with salt.
Now is the time to begin the risotto process. Using a cup to scoop from the other pot, add about 3/4 cup of the warm butternut broth to the rice. Stir to combine the broth with the rice. You'll see the rice being to absorb the broth and thicken. This is due to both "agitating" the starches of the rice through stirring, and through absorption of the liquid. The liquid should be gone after about 2-3 minutes, add another scoop and continue to repeat the process.
Stir, add broth, and stir for the next 15-25 minutes or so. When you are almost done with your broth, and when the rice looks like it has doubled in size, begin to taste. You want the rice to be soft, cooked through and not chalky in the center. You might not need all the broth to get to this state, so taste early and be sure not to overcook!
When the risotto is ready, remove it from the heat and gently stir in the heavy cream. It will continue to thicken as it is off the heat, so make sure it's more liquidy than you plan for when you take it off the heat.
Transfer to your preferred serving dish and top with freshly grated parmesan and black pepper. Serve warm!