Preheat the oven to 425 degrees F. Place the cubed squash on a parchment-lined baking tray and sprinkle evenly with salt and pepper. Add the olive oil and use your hands to toss everything to combine. Bake in the oven for 30 minutes. After 30 minutes of baking, add the shallot to the squash and continue to bake for another 30 minutes. This will ensure the shallot doesn't overcook in the oven. Once cooked, remove from the oven as set aside.
Next, make the bechamel. Heat a small pot over medium-high heat. Add the butter and let it fully melt before adding the flour. Use a whisk to combine the butter and flour and cook for 2-3 minutes to remove the flour taste. Next add the chopped garlic and cook for an additional 30 seconds.
Add 1/2 cup of milk at time to the pot, whisking to fully combine before adding more. This will ensure that the bechamel remains smooth and there will be no lumps. Continue this process until all the milk is added, then reduce the heat to low. Add in the ground nutmeg, pepper, bayleaf and 2 cups of Parmesan cheese. Mix until the cheese is fully melted, then remove from the heat and set aside for later.
Bring a large pot of water to a boil and add 1 tsp of salt. Add the pasta to the boiling water and cook until al dente, about 10-12 minutes. Halfway through cooking, reserve 3/4 cup of pasta water for later use. Once the pasta is al dente, add the kale to the pot, stir, and then drain the pasta and kale.
To make the sauce, add the butternut squash, shallot and bechamel to a food processor and puree until smooth. While blending, pour in the reserved pasta water to loosen the sauce. Add additional water as needed.
Place the drained pasta and kale back into the pot and add in the butternut squash sauce. Toss to combine.
You can enjoy the pasta as is, or bake it. To bake, place the pasta in an 8x8-inch baking dish that is lightly greased with olive oil. Top with 1 cup of Parmigiano Reggiano cheese and broil at 500 degrees F for 2-3 minutes until bubbly and golden.
Serve on its own or paired with Blue Grouse Winery's Quill Q Red wine. Enjoy!