Preheat oven to 400ºF. Cut the top and bottom off of squash to create a flat surface, then cut squash in half to create to "bowls". Discard the seeds (See Notes). Pour 2 TB olive oil over the flesh of the squash and sprinkle with fresh ground pepper. Roast flesh side up for 40 minutes. Remove from oven and allow to cool once finished.
While the squash is roasting, heat 1 TB olive oil on medium heat in large non-stick skillet. Cook shallots 3 minutes until translucent.
Combine pepper, rosemary, mushrooms and cook for an additional 2 minutes. Add garlic and cook for 30 seconds, until fragrant.
Add turkey to mixture and cook 5-6 minutes until no longer pink.
Mix in the cranberries, breadcrumbs, and asiago until combine and the cheese has melted. Sprinkle in parsley and remove from heat.
Place 1 C of filling into the acorn squash, plus extra to create a rounded top. Sprinkle asiago cheese on top and cook in 400ºF oven for additional 20 minutes. Enjoy!