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Preheat the oven to 350 degrees F (175 degrees C).
Cut top ¼-inches off garlic cloves; brush with a small amount of olive oil. Wrap in aluminum foil.
Bake in the preheated oven until garlic is tender and browned, about 45 minutes. Cool until safe to handle, about 5 minutes; chop.
Heat 2 tablespoons olive oil in a 5-quart pot over medium-high heat. Add onion and garlic; sauté until onion is translucent, about 5 minutes. Add butternut squash and broth; season with salt and black pepper. Bring to a boil, reduce heat, and simmer until squash is soft, about 30 minutes. Cool soup about 30 minutes.
Fill blender halfway with soup; add ½ cup almond milk. Cover and hold lid down with a potholder; pulse a few times before leaving on to blend for 1 minute. Pour into a pot. Repeat with remaining soup and almond milk. Warm soup over low heat until heated through, about 3 minutes.