Preheat the oven to 400 degrees. Line a baking sheet with parchment paper.
Scoop out the seeds of the butternut squash halves.
Brush the olive oil on the insides of the butternut squash. Place face down on the lined baking sheet.
Roast for 30 minutes.
Remove the pan from the oven and add the shallot halves and the garlic cloves to the baking sheet, both brushed with the remaining olive oil.
Immediately place back in the oven and roast for another 15 minutes.
Remove from the oven and leave the roasted vegetables until they are cool enough to tough—between 5 to 10 minutes should be fine.
Scoop out the butternut squash flesh and place in a blender with the roasted shallot and the garlic cloves (press out of the peels). Discard the garlic peels and the squash skins.
Add the chicken or vegetable broth to your blender. Sprinkle in a dash of black pepper.
Blend until smooth—about 20 seconds.
Pour the soup contents into a stockpot and turn the heat on medium-low.
Add in the half-in-half, stir to combine.
Let the soup fully heat through before serving! Top with pumpkin seeds, if desired.
Notes
Calories account for 1 bowl. If you are using this soup to serve 8 small servings, calories would be around 79 calories per.