Preheat oven to 400°F.  Fully line two rimmed baking pans with parchment paper.

Arrange the tomatoes, onion, and red bell pepper in a single layer on the lined baking pans.  Drizzle the olive oil over the tomato mixture.  Season with the salt and pepper.

Roast the tomato mixture in the preheated oven for 30 minutes; add the halved garlic.  Continue roasting until the mixture is tender, an additional 15 minutes.

Meanwhile, bring broth to a boil in a large pot or dutch oven.  Reduce heat and simmer, covered.

When ready, place half of the roasted tomato mixture into the blender. Cover and hold lid down; pulse a few times before leaving on to blend until smooth, adding a small amount of the warm broth if extra liquid is needed. Pour pureed tomato mixture into the pot with the broth. Puree remaining half of tomato mixture and add to stock mixture, mixing well. Simmer for 5 minutes until heated through.

Alternatively, the roasted veggies can be transferred directly to the hot broth.  Using an immersion blender, process until the entire mixture is smooth.  Simmer for 5 minutes to be sure it is heated through. 

Stir in the chopped fresh herbs.  For a creamier consistency, add half & half or heavy cream to taste.  Or serve the soup as it is with the cream on the side to be added, if desired, to individual servings.