Preheat oven to 400°. Line a baking sheet with parchment paper and set aside.
Add cubed butternut squash to a mixing bowl along with olive oil (or vegetable broth for the oil-free option) plus salt and pepper to taste. Stir to combine.
Transfer the butternut squash to the parchment-lined baking sheet. Bake for 15 minutes. Carefully stir the butternut squash pieces and return to the oven. Bake for another 15 minutes.
When the squash is nearly done, add chopped onion and wine to a 3- or 4-quart soup pot. Cook the onion over medium heat until translucent, approximately 5-7 minutes, stirring frequently.
Stir in sage, thyme and butternut squash. Cook for 5 more minutes, stirring frequently.
Add vegetable broth and bring to a boil. Once boiling, cover and reduce heat to a simmer. Cook for 20 minutes.
Remove from heat, uncover and let stand 5 minutes.
Using an immersion blender, puree mixture until no chunks remain, being careful not to splash hot liquid.
Stir in plant-based half & half. Cook for 5 minutes over medium heat, stirring occasionally.
Season with additional salt and pepper to taste.