Nothing says "holiday meal" to me like a centerpiece-worthy platter of roasted meat and vegetables. The season requires that you have options, because you might be cooking for a crowd or a dinner party. I like to make a little extra of this particular recipe, and use the leftovers for sandwiches. What could be better?
Season the pork loin with 1 tablespoon of salt and a generous amount of black pepper. Chop the garlic and sage together to make a coarse rub for the pork. Rub it into the pork loin. Cover with plastic and refrigerate for a few hours, preferably overnight. Remove it from the refrigerator 30 minutes before you're going to cook. (Note: Please allow 8 hours for overnight marinating.)
Preheat the oven to 425 degrees F. Set a medium sauté pan over medium-high heat. Add the bacon to the pan, and fry until crisp and fully rendered. Transfer the bacon to a paper towel-lined plate with a slotted spoon. Return the pan to the heat.
Add the orange juice, maple syrup, apple cider vinegar, and chili powder to the sauté pan with the rendered bacon fat. Simmer the glaze until it thickens and becomes syrupy, about 2–3 minutes. Once the glaze has thickened, drizzle in a tablespoon of olive oil, for added body and glossiness. Set aside.
Trim, clean, and halve the Brussels sprouts. Spread them out on a rimmed baking sheet. Set aside.
Peel and cut the butternut squash into quarter-moon shapes, ¼-inch thick. Spread out on a second rimmed baking sheet. Set aside.
Remove the plastic wrap from the rested pork loin, and discard. Brush the sage/garlic mixture off and place the loin, fat side up, on the third rimmed baking sheet. Drizzle half of the cooled glaze over the pork loin, smearing it in with your hands. Coat the vegetables in the remaining olive oil, scatter a few sprigs of thyme on the trays, and season with salt. Toss with the remaining glaze. Place the trays in the oven and set a timer for 10 minutes.
Check the vegetables after 10 minutes; remove from the oven once they're golden brown and slightly soft in the middle. Drop the oven's temperature to 375 F and continue roasting the pork loin until an instant-read thermometer inserted into the thickest end reads 140 degrees F, about 20–30 minutes. Remove from the oven and let rest.
Spread the roasted vegetables on a large serving platter. Slice half of the pork loin, and arrange on top of the vegetables. Garnish with the cooked bacon and lemon wedges. Serve immediately.