Preheat the oven to 400ºF. Toss butternut squash with one tablespoon olive oil and arrange in a single layer on a large baking sheet. Season with salt and pepper. Roast squash in the oven, stirring once or twice, until soft and beginning to brown, about 30 minutes. Set aside.
Meanwhile, bring vegetable stock to a boil in a medium pot, then reduce heat to medium low and allow to simmer.
In a large pot, heat 3 tablespoons olive oil over medium heat. Add shallots and cook, stirring, until softened, about 5 minutes. Add garlic and cook, stirring, for one minute.
Add the rice and stir to coat with the shallot mixture. Add the wine, stir, and allow to simmer for a minute. Add one ladleful of the simmering stock to the rice and stir. Stirring continuously, keep adding a ladleful of stock to the rice as soon as the rice absorbs the last addition. Continue this for twenty minutes. When it is almost done, add the remaining two tablespoons of olive oil.
Remove the rice from the heat and gently fold in Parmesan cheese, kale, and roasted butternut squash. Serve immediately, with additional Parmesan cheese if desired.
Tips for customizing your butternut squash risotto
Add toasted pine nuts to the top
Substitute spinach or another leafy green for the spinach
Swap the butternut squash for another type of squash or sweet potato
If you prefer not to cook with alcohol, replace it with more vegetable stock
Leave out the parmesan cheese, add a scoop of butternut squash puree, or use a vegan parmesan to make this a vegan butternut squash risotto