Preheat the oven to 425 degrees Fahrenheit.
Add the cubed squash, pears, salt and pepper and thyme to a baking sheet and toss with olive oil until everything is evenly coated.
Roast the squash and pears for 40 minutes until the squash and pears are tender and cooked through.
Meanwhile, bring a soup pot to medium heat and drizzle with olive oil.
Once hot, add the diced shallot and sauté for 2-3 minutes until softened but not caramelized.
Add the chopped garlic and spices and sauté for another minute until fragrant.
Once the squash and pears are done, remove the thyme stems and discard. Add the roasted squash and pears to the pot and pour in the vegetable stock and simmer the soup for 10-15 minutes, so all the flavors come together.
Turn off the heat and use an immersion blender (or you can ladle the soup into a blender) and blend until completely smooth.
Pour the heavy cream in and give the soup a good stir. Taste for seasoning and adjust as needed.
Serve the soup in bowls and garnish with a drizzle of olive oil and fresh thyme leaves.