Cut the squash in half length wise and scrape out seeds. Brush the cut side of the squash with a little olive oil, season with salt and pepper. Arrange on a baking sheet or dish. Set aside.
Brown the sausage, remove from pan. (depending on how lean your chicken sausage is, you may need to add some oil to the pan to keep it from sticking or burning. Mine did not need any oil. Just keep an eye on it).
Heat olive oil, sauté onions and bell pepper with a little salt and pepper until soft and golden 7-10 minutes. Add garlic and cook for about 30 seconds, until fragrant, being careful not to burn.
Add wine to pan and deglaze, scraping up the brown bits on the bottom.
After pan is deglazed, add sausage back into the pan, as well as the rice, oregano and red pepper flakes, kosher salt and pepper to taste ( how much you add will depend on how hot the sausage you use is, as well as how salty.
Cook until everything is mixed and heated through.
Divide the mixture between the squash.
Cover the squash with foil and bake for about 40 minutes. Uncover and bake another 20 minutes or until squash is tender.