Preheat oven to 400F and line 2 baking sheets with parchment paper.
Cut squash in half lengthwise and then again in half width-wise (see image above). Peel squash and remove seeds (if you would like to roast them, see step 8)
Place on one of the baking sheets and brush with 1 tbsp olive oil and 1/4 tsp of salt and pepper each.
Peel and chop carrots into 1/2 inch pieces (see image above). Chop pepper into eights, quarter the onion and peel the garlic.
Add to a bowl with 1 tbsp olive oil, 1 tsp oregano, 1 tsp basil, 1/2 tsp smoked paprika, 1 tsp thyme, 1/4 tsp salt and 1/4 tsp pepper.
Toss to coat evenly.
Spread on the remaining baking sheet. When there are 25 minutes left of your timer (or squash has been in for 35 minutes) add to the oven.
If you would like to roast the squash seeds, clean them and pat dry with paper towel. Toss with 1 tsp olive oil and some salt and pepper (or any spices you'd like) and add them to the oven at this point. Remove when you remove the veggies (but keep an eye on them!)
Once veggies are done, remove from oven and add to a large pot with 5 cups of vegetable broth. You will likely have to break up the squash into smaller chunks
Bring to a boil, cover and simmer on low for 35 minutes.
Allow to cool for 5-10 minutes and purée with an immersion blender until smooth.
Add 1/2 cup cream and stir to incorporate.
Season with additional salt and pepper, squash seeds and fresh herbs.