Preheat oven to 425°F.

Boil penne pasta per package directions, until just tender. Set aside in water.

In a fry pan, brown sausage and onion, and garlic. Drain and return fat to pan. Transfer sausage to large bowl. 

Add olive oil to fry pan and sauté squash until edges are brown. Add squash to sausage. 

Drain pasta. Add to sausage and squash. Add sage, rosemary, cinnamon, red pepper flakes. Toss lightly to mix.

Pour vinegar and Worcestershire in fry pan, heat on low to medium and scrape to deglaze. Add liquid and bits to sausage mixture. Toss lightly.

Transfer to a large casserole. Bake for 15 to 20 minutes, or until top is browned and squash is tender. (To retain moisture, bake with lid on casserole.)

Serve with Parmesan cheese.