Preheat the oven to 400°F (200°C). Halve the butternut squash lengthwise, scoop out the seeds, and place the halves cut-side up on a lined baking sheet.
On the same baking sheet, place the cherry tomatoes, carrots, onion and the garlic bulb. Drizzle everything with olive oil and season with salt, pepper, and a pinch of smoked paprika.
Roast for about 40-45 minutes, or until the squash is fork-tender and lightly browned on top.
Let the squash cool slightly, then scoop the flesh out of the skin and add it to a pot along with the roasted tomatoes, carrots, onion, and garlic.
Add 2 to 3 cups of vegetable broth (start with 2 cups, then add more as needed to reach your desired consistency). Bring the mixture to a gentle simmer.
Once everything is warmed through, blend the soup until smooth. If the soup is still too thick, add extra broth in small increments until it reaches your desired texture.
Stir in the cooking cream, adjust seasoning as needed, and serve with a drizzle of pumpkin seed oil, and cream.