Preheat the oven o 380F and line a baking tray with parchment paper. You will also need a 9"x13" baking dish for this recipe.
Prepare the butternut squash by using a peeler to remove its outer skin. Cut it in half lengthwise. Clean out the cavities with a spoon. Cut the halves into slices and then chop them up into 1-2 inch cubes.
Prepare the garlic bulbs by cutting off the top tip of the bulb, just enough to expose the cloves. Place them cut side up on the lined sheet pan, with the cubed squash, prepared carrots, bell pepper, and onions.
Drizzle the veggies generously with olive oil and sprinkle with salt.
Bake the tomatoes
Cut the Roma tomatoes lengthwise. Place them cut side up in a 9"x13" baking dish.
Drizzle the sliced tomatoes with olive oil. Sprinkle with salt and the dry oregano.
Cook the Soup
Place the baking tray of veggie and the dish of tomatoes into the preheated 380F oven. Bake for 1 hour. Remove the roasted veggies from the oven and let them cool for 15-20 minutes.
Remove the garlic bulbs from the tray. Transfer the roasted carrots, onion, bell pepper, squash, and tomatoes to a soup pot. Take the garlic bulbs and squeeze them to remove the cloves and place them in the pot with the veggies.
Pour the broth into the soup pot with the veggies. Bring to a simmer and cook on low for another 15-20 minutes to really blend all the flavors together.
Use an immersion blender to blend the soup until smooth. Taste the soup and adjust the seasoning to your preference. If using low sodium broth, you might need to add more salt.
Serve the soup with freshly grated parmesan cheese, and or croutons.