Preheat the oven to 375F. Wash the squash well, then dry with a towel. Trim the top and bottom off each squash, then cut in half from top to bottom. Use a melon baller or spoon to remove the inner seeds and strings. Then cut into half again. Place on a lined baking sheet.
Whisk the bourbon maple syrup ingredients together with the maple syrup, olive oil, pumpkin pie spice, cayenne pepper, and salt until well incorporated. Brush the maple bourbon mixture onto both sides of the squash. Roast for 20 minutes. Then roast the squash for 25 minutes on the first side, then flip each slice over and bake for another 15 minutes, until caramelized and soft.
In the meantime simmer the cranberries, orange juice, and the cherry port over medium heat until simmering then low heat for Set aside. Prepare the whipped goat cheese by blending all the ingredients in a medium-size bowl with hand mixer. Set aside.
Place the acorn slices on a serving platter. Scoop a tbsp of whipped goat cheese. Garnish with cranberries, pomegranate seeds, candied pecans, and fresh thyme.