Preheat the oven to 400 degrees F.

Place the cubed butternut squash on a large baking sheet and drizzle with olive oil. Season with salt and pepper, to taste. Roast for 25 to 30 minutes or until soft and tender, but not mushy. Remove from oven and drizzle with maple syrup and gently stir. Set aside.

Bring a large pot of water to a boil. Meanwhile, in a large Dutch oven or pot, cook the sausage over medium-high heat, stirring occasionally, until it's browned. If there's a lot of excess fat, drain most of it. Transfer the sausage to a plate that has been lined with a paper towel. Set aside.

Salt the boiling water generously and cook the tortellini according to package instructions. Drain and set aside.

In the same Dutch oven or pot, heat the olive oil over medium heat. Add the shallot and cook until tender, about 3 minutes. Add garlic, sage, and crushed red pepper flakes and cook for 1 minute.

Pour in the chicken broth and bring to a boil. Reduce heat and simmer for 2 to 3 minutes. Stir in the heavy cream and stir until sauce thickens, about 3 to 5 minutes. Stir in the Parmesan cheese.

Add the sausage and tortellini to the sauce and stir until well coated. Gently stir in the roasted butternut squash. Season with salt and pepper, to taste.

Serve warm with extra parmesan cheese, sage, and crushed pepper flakes.