Brown the bacon. Bring a large pot of water to a boil. Meanwhile, add the oil, butter, bacon, and smashed garlic to a large skillet over medium heat. Cook for about 6 minutes, stirring occasionally, until the bacon is golden. Adjust the heat as needed to keep the garlic and butter from burning.
Grate the pumpkin and cook the pasta. While the bacon cooks, coarsely grate the peeled and seeded pumpkin. Once grated, add the fusilli to the boiling salted water. Cook according to the package directions until al dente. Reserve at least 1 cup of pasta cooking water before draining.
Cook the pumpkin. Add the grated pumpkin to the skillet with the salt, black pepper, and dried basil. Cook for 3 minutes, stirring frequently.
Make the sauce. Add ½ cup of the pasta cooking water, the white wine, and heavy cream. Stir well and simmer gently for 3 minutes, stirring occasionally, until the pumpkin is tender.
Stir in the Parmesan. Reduce the heat to low. Add the finely grated Parmesan and stir until melted and incorporated into the sauce.
Add the pasta and serve. Add the drained fusilli and toss until evenly coated. If needed, loosen the sauce with a small splash of the reserved pasta water. Serve warm with extra Parmesan, if desired.