In a large stockpot, heat the oil over medium heat. When it simmers, add the onion and season with a pinch each of salt and pepper. Cook, stirring frequently, for about 5 minutes, until softened. Slowly add 1/2 cup of the cider and let it cook into the onions. Repeat until all the cider has been added and the onions are caramelized, about 10 minutes total. Add the apples, squash, and thyme and cook over medium heat, stirring, until softened, about 8 minutes. Add the beer, 3 cups of the broth, and the cayenne. Increase the heat to high, bring to a simmer, and cook for 15 to 20 minutes, or until the apples and squash are tender.
MEANWHILE, MAKE THE GRANOLA. In a large skillet, cook the bacon over medium heat until crisp, 3-4 minutes per side. Drain on a paper towel-lined plate. When cool enough to handle, coarsely crumble the bacon.
In the same large skillet, melt the butter over medium heat and cook until just beginning to brown and smell toasted. Add the oats and pumpkin seeds and cook for 1 minute more. Remove the skillet from heat and stir in the crumbled bacon. Season with salt.
When the apples and squash are tender, transfer the soup to a blender and pulse until smooth.
Return the soup to the pot and set over medium heat. Stir in the milk, then bring the soup to a low boil. Stir in the cheddar and Brie until melted and smooth. Add more broth to thin the soup, if desired. Simmer for about 5 minutes more, or until ready to serve.
Ladle the soup into bowls and top with the granola.
Recipe from: Gerard, Tieghan. Half Baked Harvest Cookbook: Recipes from my barn in the mountains. New York: Clarkson Publishers, 2017. p. 248.