Preheat the oven to 400 degrees F.
Take the cubed butternut squash and spread out on a baking sheet. Toss with a little olive oil, salt and pepper. Put in the oven to bake for 35-40 minutes, stirring every 15 minutes. Squash will be done when soft in the middle and slightly caramelized on the outside.
In a large pot, add water for pasta and start heating up. Once water is boiling, add a bit of salt and pasta to the pot, and cook according to package directions.
While pasta water is heating up, take two slices of thick cut bacon and cut into small pieces. Cook in a skillet over medium heat until cooked through, but not too crispy. Remove from the pan and drain on paper towels until ready to use.
Once the butternut squash, pasta, and bacon are all done, get prepared to assemble.
Drain the pasta and drizzle with olive oil. Mix until pasta is well-coated, but not swimming in oil. Add more oil if needed. Add dried sage and salt and pepper to the pasta and mix.
Divide the pasta between the bowls and then top with the bacon and butternut squash. Grate or shave parmesan cheese over the top and top with any other fresh herbs.