On a parchment-lined baking sheet, toss the butternut squash cubes with 1 tablespoon maple syrup, 2 tablespoons olive oil, and salt and pepper to taste. Roast in the oven for 20 minutes, until tender and caramelized. Set aside.
In a large bowl, thoroughly combine the cornmeal, flour, baking powder, sugar, and salt. In a medium bowl, whisk together the buttermilk, eggs, butter, and ¼ cup maple syrup. Gently fold the wet ingredients into the dry ingredients just until combined. Gently fold in the cooked butternut squash cubes, herbs, chopped bacon, and 3/4 cup grated cheese. (You can save some of the squash, bacon, and herbs to top the muffins with as well).
Line your muffin pan with paper cups and fill the cups about 2/3 of the way full. Top the muffins with the remaining ½ cup of cheese and any of the reserved squash, bacon, and herbs. Bake for 16-18 minutes, until a toothpick comes out clean.