Preheat oven to 400°. Line a cookie sheet with parchment paper and add your chopped butternut squash, drizzle olive oil over and carefully toss to coat. Sprinkle salt and pepper over. Roast in preheated oven for 30-45 minutes, until golden brown.
While butternut squash is roasting, cook pasta according to package. Drain and set aside.
On medium-low heat in the same pot you used for the pasta, add and melt your butter, milk, cheeses, paprika and nutmeg.
After the cheese has melted, either add the drained pasta back into the dutch oven or a casserole dish and stir to combine. Then carefully toss your butternut squash into the dish. If you'd like to "hide it" stir a little more. Sprinkle with salt and pepper.
Bake in a preheated 375° oven for 20 minutes, until the top is golden brown. Enjoy!