Add squash, brussels sprouts, apples, and shallots to a large bowl.
Toss in 2 tbsp of oil and season with salt and pepper to your taste.
Place vegetables on a sheet pan in the oven and roast until veggies are tender (about 40 minutes).
Reduce heat to 350°.
Heat other 3 tbsp of oil in a large pot and add the onion and celery. Cook down until translucent (about 8 minutes or so).
Add the cornbread cubes to the onion and celery, allowing them to brown with the veggies for a few minutes.
Add the roasted veggies, vegetable broth, cranberries, pecans, nutritional yeast, and herbs to the pot and stir to combine. Allow the broth to be almost completely absorbed into the bread.
Transfer mixture to a baking dish and bake at 350° for 20 minutes.
