Preheat the oven to 425. On a cookie sheet, toss the squash with a liberal pour of olive oil (about 1/4 cup), salt and pepper, and spread out. Roast, tossing halfway through, until tender and caramelized but not mushy; 30 to 35 minutes (mine was done closer to 20, probably because I cut the squash a little smaller).
Bring a large pot of water to a boil over high heat.
Heat another large pot over medium-high heat. coat the bottom of the pan with a thin layer of olive oil. Add the sausage, and cook, breaking up the meat into bite-size chunks, until browned, 6 to 8 minutes. (The sausage won’t be fully cooked.)
Reduce the heat to medium and add the garlic, shallots, and nutmeg. Cook, stirring occasionally, until the shallots are translucent and the garlic is soft, 3 to 4 minutes.
Deglaze the pan with the wine, and scrape up any brown bits from the bottom of the pan. Cook until the wine is reduced by half, 1 to 2 minutes.
Add the cream, bring to a simmer, and reduce the heat to very low to keep the sauce warm while the pasta cooks, about 10 minutes.
Generously salt the boiling water and drop in the rigatoni. Cook according to the package directions until al dente. Lift the pasta with a spider tool into the pot with the sausage.
Add a splash of pasta water and pecorino Romano to the pot, and toss to combine. Cook, adding splashes of pasta water as needed, until the sauce coats the pasta nicely, 1 or 2 minutes. (I cooked it down until all the liquid was absorbed, but that’s just me.)
Turn off the heat, and gently stir in the squash. Season with salt and pepper. Serve, topped with more pecorino Romano and a small grating of fresh nutmeg.