- Preheat oven to 375 degrees.
- Place squash in single layer on sheet pan and drizzle with olive oil. Cover pan with foil and place in oven. Bake until squash are fork tender, approximately 45–50 minutes.
- In medium bowl, place flour, cinnamon, brown sugar, pecans, bacon, ¼ cup melted butter, and sorghum. Stir to combine until mixture is clumpy. Set streusel aside.
- Place chicken stock in small pot and warm over low heat.
- Place squash in large bowl. Use potato masher to mash until smooth. Stir in 5 tablespoons cubed butter, then add warm chicken stock and stir to combine. Season with salt to taste.
- Reduce oven to 350 degrees.
- Pour squash mixture into 10×7 or 2½-quart baking dish. Sprinkle streusel over top. Place in oven and bake until streusel is golden brown, approximately 45 minutes.