Add your cut and cleaned carrots (not the green tops) and cut and halved acorn squash to a sheet pan and drizzle with olive oil and sprinkle with salt and pepper.
Roast your vegetables for about 20-25 minutes or until they start to brown a little and are soft all the way though
Once cooked, remove from the oven and let cool for a minute before handling
In the meantime, heat a large heavy bottom pot over medium heat and add ½ of your olive oil
Now add your diced shallots and 1 clove of your minced garlic and cook for about 4-5 minutes
Now add your chicken stock, thyme and bay leaf
Now we are going to get the roasted vegetables ready to add to the pot by scooping the flesh of the acorn squash away from the skin. You may be able to just peel the skin of the squash right off.
Once this is done, you can add your whole carrots and the flesh of the squash right into your soup.
You can mash it down a bit with the back of your spoon. Don't worry about smoothness here since we will be pureeing it all in a blender.
Now add your salt, pepper and your cream
Mix it well and let it come to a light simmer
Once it has simmered for a few minutes, remove your bay leaf and discard.
Bring your pot over to the blender (If you have an immersion blender, you can just puree your soup right in the pot and skip the blender steps)
Add your soup to the blender making sure to only fill it ¾ of the way to the top as hot soup will expand in the blender
Place the top on your blender tightly and cover with a towel. Puree your soup on high for 2 minutes or until smooth
You may need to do this in batches to make sure you do not over fill your blender
Once your soup is all blended and smooth, add it back to your pot. Taste for any seasoning (add salt and pepper to taste) then place over low heat with a lid on top.
Carrot top pistou (carrot top pesto)
Take the green tops from your carrots and finely chop them
Add this to a food processor along with the remaining ⅛ cup of olive oil, 1 clove of minced garlic and your Parmesan cheese and blitz until it is smooth.
Add your pistou to a small bowl
Ladle your soup into bowls and top with a dollop of the pistou
For making a more traditional Italian pesto with the carrot top greens:You can add ½ cup of nuts (almonds or walnuts) and 2 more tablespoons of olive oil to the pesto recipe and mix in the food processor until somewhat smooth.