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Bring a large pot of generously-salted water to a boil.
Meanwhile, heat the butter in a separate large sauté pan until melted. Add the sage leaves (if using) and sauté for 1-2 minutes until crispy. Transfer the sage leaves to a separate plate and set aside.
Add the garlic and sauté for 1 minute, stirring occasionally. Then add in the butternut squash and vegetable stock and stir to combine. Continue cooking until the stock reaches a simmer. Reduce heat to medium-low, cover and cook for 10 minutes, stirring occasionally, until the squash is tender and mashes easily with a fork.
Transfer the squash mixture to a blender. Add in the milk and give the mixture a quick stir. Then very carefully (I recommend slightly opening the cap on the blender lid, so that excess steam can escape) pulse the mixture until smooth.
Add the pasta to the boiling water and cook according to package instructions until al dente. Reserve 1 cup of the starchy pasta water for later. Then drain the pasta.
While the pasta is cooking, return the butternut squash mixture back to the sauté pan over medium-high heat. Add in the shredded cheddar cheese, and stir until it has melted into the sauce.
Taste and season the sauce with salt and pepper as needed. (I used about 1 teaspoon salt and 1/2 teaspoon black pepper.)
Then once the pasta is drained, return it to the stockpot. Pour the butternut cheese sauce on top of the pasta, and toss to combine. If the sauce is too thick, add in some of the hot starchy pasta water to thin it out.
Serve warm, garnished with the crispy sage leaves if desired.