Preheat oven to 350 degrees. Line a baking sheet with parchment paper.

Cut the top third of the squash off and remove the seeds with a spoon. Cut a flat spot on the bottom of each squash so they sit flat. Place squash bowls on prepared baking sheet, cut side up.

Add a clove of garlic to each squash bowl. Drizzle with 2 Tbsp of olive oil and season with 1 Tbsp salt and 1 Tbsp black pepper.

Roast in the oven until very tender, just before the sides begin to collapse, approximately 1 hour. Remove from oven and when cool enough to handle, remove the squash and garlic cloves from the bowls, leaving enough to allow the bowls to stand up (leaving approximately 1/4 to 1/2-inch border of squash all around.

In a large Dutch oven or heavy-bottomed pot, heat 1 Tbsp of olive oil and 2 Tbsp of butter on medium-high heat. When the butter begins to foam, add onion and ginger, and cook until the onion is tender, approximately 5 to 6 minutes.

Stir in 1/2 cup of the chicken stock and scrap the bottom to remove any bits. Reduce heat to medium-low and add the squash, garlic, and remaining chicken stock. Stir to combine.

Puree mixture with a stick blender. The mixture will be thick. Stir in cayenne, sage, oregano, vanilla, heavy cream and 2 Tbsp of butter. Heat slowly.

When the soup reaches a simmer, mix again with the stick blender and stir in the Parmesan cheese. Reduce heat to low and stir until the cheese is melted. Keep warm until ready to serve.

Ladle the soup into the acorn squash bowls when ready to serve. Garnish with fresh sage leaves.