Preheat oven to 400 degrees F. Line a baking sheet with parchment paper.
Place butternut squash onto prepared baking sheet. Add 2 tablespoons olive oil and gently toss to combine. Place into oven and roast until softened and cooked through, about 40 minutes.
Heat remaining 1 tablespoon olive oil in a large stockpot or Dutch oven over medium heat. Add garlic and shallots, and cook, stirring occasionally, until caramelized, about 15-20 minutes. Stir in vegetable broth and red ale and bring to a boil; reduce heat and simmer for 5 minutes.
Remove from heat and stir in butternut squash, salt, pepper, cayenne pepper and heavy cream. Puree with an immersion blender; season with salt and pepper to taste.
Return to heat and bring to a simmer until slightly thickened, about 10 minutes. Add more vegetable broth until desired consistency is reached.
Serve immediately, garnished with goat cheese and pomegranate seeds.