Preheat your oven to 450° F. Cut your butternut squash in half, lengthwise by spearing your squash in the middle and gently (and slowly) pressing down on the knife with the heel of one hand, while holding the gourd with the other hand. Repeat this until the entire squash is cut in half. Rub the top of the flesh with 1 tbsp olive oil (skip if you want this to be oil free). Season with 1/2 tsp salt and 1/2 tsp black pepper, as well as 1 tbsp of Italian seasoning. Place the two halves on a sheet pan, flesh side up.
Slice the garlic head in half (around the middle) and wrap it in foil. Place it on the same sheet pan as the butternut squash.
Place the apple, fennel, carrots, and shallots on a separate sheet pan, lined with parchment paper. Drizzle with olive oil (or veggie broth if you want it oil free), and season with remaining salt and pepper and Italian seasoning. Place both sheet pans in the preheated oven. Remove the vegetable sheet pan at around 35 minutes (when apples are browned) and the squash sheet pan at 55 to 65 minutes (when squash is fork tender). Allow everything to cool to room temperature.
Remove the seeds from the squash by using kitchen shears and a large spoon. Then, scoop out all the flesh and place in a high-powered blender, together with roasted veggies and fruit, and roasted garlic. Add miso paste, maple syrup, and 4 cups of vegetable broth. Blend on high until silky smooth. If too thick, add additional vegetable broth. When serving, garnish with fennel fronds, toasted pumpkin seeds, a little vegan cheese, and a quick drizzle of olive oil. Maybe even another turn of that cracked black pepper!