Cut the squash. Place a rack in upper third of oven; preheat to 425°F (220°C). Halve squash lengthwise and scoop out seeds with a large spoon. Using a peeler, remove skin and white flesh below. Drizzle with 1 Tbsp olive oil, then season with ½ tsp Kosher salt and a pinch of black pepper.
Roast butternut squash. Roast in a baking dish just large enough to hold halves side by side until beginning to soften (a paring knife should easily slip in only about ¼-inch), 15-18 minutes.
Make the glaze. Combine 4 Tbsp butter, ¼ cup apple cider vinegar, and 2 Tbsp maple syrup in a small sauce pan over medium-high heat, stirring occasionally. When butter has melted and sauce begins to boil, add 8 large sage leaves, 2 smashed and peeled garlic cloves, and ½ tsp ground cinnamon. Cook for 5 minutes, then add 2 Tbsp bourbon. Cook for 1 minute more, then turn heat down to lowest setting.
Cut the squash. Transfer squash to a cutting board and let cool slightly. Using a sharp knife, score rounded sides of squash halves crosswise, going as deep as possible but without cutting all the way through. Return squash to baking dish, scored sides up, and tuck 10-12 sage leaves and 2 thinly sliced garlic cloves between a few of the slices; season with salt and pepper.
Cook the squash. Roast squash, basting with glaze every 10 minutes or so and using a pastry brush to lift off any glaze in dish that is browning too much, until tender and glaze forms a rich brown coating, about 45 minutes.
Finish assembling and serve. In a medium bowl, combine ½ cup panko, ¼ cup Parmesan, 1 tsp Kosher salt, ½ tsp black pepper, and 2 tsp olive oil. Sprinkle panko breadcrumb mixture evenly on top of both butternut squash halves. Return to oven and cook for an additional 5-7 minutes, just until panko has browned. Top with ¼ cup crushed pecans, 2 thinly sliced scallions, and ⅓ cup crumbled goat cheese. Serve immediately!