Preheat oven to 425 degrees F (220 degrees C).
Peel and chop the Butternut Squash (1 pound) into cubes.
In a bowl, combine the butternut squash with Olive Oil (2 tablespoon), Kosher Salt (1 teaspoon), and Freshly Ground Black Pepper (1/2 teaspoon). Stir to coat.
Spread the squash on a baking sheet and roast for 20 minutes, tossing half way through to evenly cook. When it’s ready, the squash will be soft and some of the edges will have browned.
While the squash is roasting, slice the Shallot (1/4 cup) and set aside.
To brown the butter, melt the Butter (8 tablespoon) in a saucepan over medium heat. Continuously stir and watch it to make sure it does not burn. The butter will start to foam and smell nutty and the color will turn amber.
Once the butter is slightly brown, add the Sage Leaves (4). Remove the saucepan from the heat as soon as the sage leaves start to curl. Set aside.
Place the Bacon (8 ounce) in a cold skillet and cook over medium heat until crispy.
Remove the bacon from the skillet and drain on paper towels.
Place the skillet back on the stove, but with the heat turned off. Keep 2 tablespoons of the bacon grease in the skillet. Add the shallots to the skillet and cook in the residual heat from the skillet; this helps prevent the shallots from burning. Transfer the cooked shallots to a large bowl.
Bring a large pot of salted water to boil and cook the Penne Pasta (1 pound) to al dente, or according to package directions.
Drain the pasta and then pour it back into the large pot.
Combine the butternut squash, shallots, bacon, and browned butter with the pasta. Stir to combine.
Divide the pasta into bowls.
Garnish with Parmesan Cheese (to taste). Enjoy!