Preheat oven to 400 degrees F, and line a large baking sheet with tin foil.

Cut butternut squash into 1-inch cubes, and place on half of the baking sheet along with the shallots. Drizzle the olive oil over the squash and shallots and then evenly sprinkle salt and pepper all. Toss together to fully coat, and then spread everything in an even layer on one side of the pan. Bake the squash for 20 minutes.

Remove the squash from the oven and stir/flip. On the other side of the baking sheet, lay out the bacon strips and return to the oven for 15 minutes more.

In the meantime, cook the penne pasta according to the directions on the box. Once the pasta is done, drain and then rinse quickly under warm water. Place the pasta in a deep serving bowl.

Once the butternut squash is done roasting, transfer it immediately into the bowl with the pasta, tossing well. Once the bacon has cooled slightly and can be handled, crumble into the bowl and add the walnuts and cinnamon. Stir everything together gently, until ingredients are evenly dispersed.

Garnish with fresh basil, to taste.