Preheat the oven to 400 degrees. 

Prep the carrots, beets, squash, and grapes for roasting. Rinse the carrots, beets, and grapes under cold water, removing dirt. Dry with a paper towel and set aside in a large mixing bowl. Add the sliced acorn squash, olive oil, salt, pepper, thyme, rosemary, cinnamon, sugar and toss lightly with your hands. Line a baking sheet with parchment paper, spread the fruit/vegetable mixture evenly onto the sheet, and roast in oven for 30-45 minutes. 

Meanwhile, heat an iron skillet over medium-high heat. Add the butter and sliced apples to the skillet and cook for 5-6 minutes or until the edges are brown. Remove apples from the pan and set aside. Reduce the heat to medium. Add the prosciutto and pearl onions to the skillet and cook for 3-4 minutes. Stir in the apples, apple cider vinegar, a pinch of kosher salt and pepper, then remove from the heat and set aside.

Once the fruit and vegetables are roasted to perfection, remove them from the oven and transfer to a serving platter. Carefully add the sauteed apples, prosciutto, and pearl onions. Sprinkle with fresh thyme and serve.