Step 1

Preheat the oven to 400 degrees F (200 degrees C). Coat a baking sheet with olive oil.

Step 2

Place butternut squash and sweet potato cut-sides down on the baking sheet.

Step 3

Bake in the preheated oven until easily pierced with a knife, 45 to 50 minutes. Remove from the oven and let sit until cool enough to handle.

Step 4

While squash and potato are cooking, heat 3 tablespoons oil in a skillet over medium-high heat. Add garlic and fresh sage and cook until garlic is browned and sage is crispy, 3 to 5 minutes. Remove sage to a paper-towel lined plate. Transfer garlic to a blender.

Step 5

Scoop out the flesh of the butternut squash and potato using a spoon and transfer to the blender with garlic. Discard squash and potato skins. Add maple syrup and 1 cup vegetable broth to the blender and process until smooth, 1 to 2 minutes.

Step 6

Strain through a sieve to remove any lumps and transfer into a large pot. Add remaining 3 cups vegetable broth, bay leaves, cinnamon stick, 1 tablespoon thyme, and salt. Bring to a simmer over medium heat, then reduce heat to low and simmer for 30 minutes. Season with pepper and sprinkle with crushed sage leaves.