Season the acorn squash. Preheat an oven to 425F. Line a rimmed baking sheet with parchment paper, then place the sliced squash on top. Drizzle with 2 Tbsp extra virgin olive oil, then season with ½ tsp Kosher salt and ⅛ tsp black pepper.
Roast the acorn squash. Cook until tender, about 20-25 minutes, flipping once halfway through.
Make the bourbon sauce. In a small saucepan, combine 3 Tbsp unsalted butter, 2 Tbsp bourbon, 1 Tbsp balsamic vinegar, 2 Tbsp chopped fresh sage, ⅛ tsp grated nutmeg, and a pinch of cayenne. Heat over medium heat until the butter has melted and the bourbon cooks off and reduces, about 4 minutes total. Note: when the alcohol heats up enough, the vapors will ignite and you'll have a small flame in the pan. This is supposed to happen! Keep cooking until the fire dies out on its own. Remove from the heat until needed.
Toast the breadcrumbs. Heat 1 Tbsp unsalted butter in a small skillet over medium heat until melted. Add ¼ cup panko breadcrumbs, then use a spatula to stir constantly until evenly toasted, about 1-2 minutes. Remove from the heat, then transfer to a small bowl.
Stir in remaining ingredients. To the breadcrumbs, add 3 Tbsp grated Parmesan cheese and 3 Tbsp toasted chopped pecans. Stir well.
Finish the squash. When the squash is fork tender, toss it in a large bowl with the bourbon sauce, then transfer to a plate or platter. Sprinkle on the parmesan panko mixture. Garnish with crumbled goat cheese, if using, then serve immediately!