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Preheat your oven to 425°F (218°C). Line a sheet pan with parchment paper.
Cut the butternut squash in half lengthwise, scoop out the seeds, and place them aside for later roasting. Peel and cut the onion into quarters. Slice the top off the garlic head and drizzle with olive oil, then wrap it in foil.
Place the butternut squash, onion, and garlic on the sheet pan. Coat with olive oil, and season with salt, pepper, sage, and thyme. Roast for 45 minutes or until the squash is fork-tender.
While the vegetables roast, rinse the squash seeds in a colander to remove the pulp. Pat dry, toss with olive oil and salt, and roast at 350°F (176°C) for 15-20 minutes, stirring halfway through.
Once roasted, remove the flesh of the squash and the garlic cloves from their skins and place in a large soup pot. Add the roasted onion and vegetable stock.
Blend the mixture using an immersion blender until smooth. If you don’t have an immersion blender, use a regular blender in batches.
Reheat the soup over medium-low heat. Stir in the heavy cream (or vegan alternative) and adjust seasonings to taste. If the soup is too thick, add more vegetable stock. If it’s too thin, allow it to simmer until it thickens to your desired consistency.
Serve hot, topped with roasted squash seeds and croutons for extra crunch.