Preheat the oven to 450 degrees.
Wash and chop tomatoes into halves, quarters or eighths, depending on size.
Peel and chop garlic. Dice the onion and pepper.
Place all of the chopped produce on the baking sheet. Sprinkle with the olive oil, salt, pepper and dried herbs.
Roast the produce for 25 minutes, stirring once after 15 minutes.
When the 25 minutes has passed, turn the oven to broil and broil for 3 minutes to get a little bit of charred color.
While the produce is roasting in the oven, peel and chop the butternut squash.
Place in a covered casserole dish with 2 tablespoons of water. Microwave on high for 10 minutes.
Drain and set aside until the vegetables are done roasting.
Bring the chicken broth to a boil, then add the roasted vegetables and steamed squash.
Blend the mixture with a hand blender until you get a creamy, smooth texture.
Add more salt and dried herbs to taste, if needed.
Top with fresh herbs, parmesan cheese or croutons, if desired.