Preheat oven to 425F. Mix the butternut squash and olive oil in a small bowl and season with salt and pepper. Spread onto a baking sheet and roast until just caramelized, about 30 minutes.
In a large, deep skillet, or dutch oven, add 1 Tablespoon of olive oil over medium-high heat. Add the garlic and shallot and cook until soft, about 3-4 minutes. Mix in the rice and lemon zest, then add the wine. Cook until the wine is absorbed.
Add 3 cups of the stock in one cup at a time, letting each cup absorb fully before adding the next, then add the last cup of stock 1/4 Cup at a time until rice is cooked as desired (I used about a 1/2 cup).
Once all the stock is absorbed, remove from heat and stir in the lemon juice, butter, and Parmesan cheese and stir to combine.
Fold in the butternut squash and serve immediately.