Preheat your oven to 375°F. Line a large rimmed baking sheet with parchment paper and set it aside.
Peel (and seed, if you’re using butternut squash) the root vegetables and squash, and cut them into 1-inch cubes. Place them on prepared baking sheet and toss with the extra virgin olive oil (no salt!).
Spread the chunks into a single layer and place in the preheated oven. Roast until fork tender (about 30 minutes). Remove from the oven and allow to cool until no longer hot to the touch.
Place the roasted vegetables in a food processor or blender. Add 1 to 1 1/2 cups (8 to 12 fluid ounces) of the chicken stock (depending upon how thick the vegetables are) and puree until very smooth and pourable. Set the puree aside.
In a large, heavy-bottom sauté pan, melt the butter. Add the gum-free flour blend, and mix to combine.
Cook over medium heat, stirring frequently, until the mixture is golden brown and nutty smelling (about 3 minutes, and it will go from very blond to golden brown and fragrant quite suddenly, so pay close attention).
Add the vegetable puree, and mix to combine. Whisk or stir until smooth.
Add 2 1/2 cups of chicken stock, and the rosemary, sage, and thyme. Whisk to combine.
Bring the mixture to a simmer over medium heat, and cook, stirring constantly, until the mixture is beginning to thicken (2 to 3 minutes).
Remove the solid aromatics, and continue to simmer, stirring frequently, until a visible trail is left behind while stirring. Add salt and pepper to taste, and stir to combine.
Add more stock to thin if serving right away, and add the optional shredded chicken. If not serving right away, allow the condensed soup to cool to room temperature before transferring to a 1-quart canning jar and storing in the refrigerator until ready to serve.