On the day before cooking, cut the cornbread, French bread and ciabatta into 1-inch cubes. Spread them out on 2 baking sheets and let them dry for approximately 24 hours.
Preheat the oven to 425 degrees F.
Drizzle the Brussels sprouts and butternut squash with olive oil in a roasting pan and roast for 30 to 35 minutes.
Meanwhile, warm up a large skillet over medium heat and add the butter and bacon pieces. When the bacon is cooked, add the celery, carrots and onions and cook until soft, 4 to 5 minutes. Pour in the chicken broth, then add the parsley, rosemary, basil, thyme, and some salt and pepper and stir until combined. Cook for a couple of minutes.
Get the cooked sprouts and squash out of the oven and reduce the temperature to 375 degrees F.
Place the dried bread cubes into a large bowl and mix them up a bit. Add the roasted Brussels sprouts, squash, pecans and dried cherries and mix.
Gradually ladle the broth mixture into the bread, tossing lightly as you go. Add a little more salt and pepper, then toss around and taste to check the seasoning. If you like it more moist, splash in more broth until it reaches the consistency that you like.
Pile the dressing into a large casserole dish and bake until golden brown on top, 20 to 25 minutes.
Preheat the oven to 450 degrees F.
Combine the cornmeal, flour, baking powder and salt in a bowl. Stir together.
Measure the buttermilk and milk into a measuring cup and add the egg. Stir together with a fork. Add the baking soda and stir.
Pour the milk mixture into the dry ingredients. Stir with a fork until combined.
In a small bowl, melt 1/4 cup shortening in the microwave. Slowly add the melted shortening to the batter, stirring until just combined.
In a cast-iron skillet, melt the remaining 2 tablespoons shortening over medium heat. Pour the batter into the hot skillet. (The batter should sizzle.) Spread to even out the surface. Cook on the stovetop for 1 minute, and then transfer to the oven and bake until golden brown, 20 to 25 minutes. The edges should be crispy!