Preheat oven to 450°F.
Combine tomatoes, celery, onion, garlic, and olive oil in an ovenproof Dutch oven.
2 lbs plum tomatoes, cored and sliced in half, 3 celery ribs, coarsley chopped, 1 onion, sliced, 1 clove garlic, minced, ¼ cup olive oil
Bake in preheated oven for 35-40 minutes, or until vegetables are tender.
Remove the vegetables from the oven and reduce the oven temperature to 400°F.
Add the chicken stock, tomato paste and basil to the roasted vegetable mixture. Stir to combine and bring to a boil over medium-high heat. Reduce the heat and simmer for 10 minutes.
2 cups chicken stock, 1 tablespoon tomato paste, ¼ cup basil, chopped
Using an immersion blender, blend all the ingredients until the mixture is smooth.
Add the whipping cream and stir to combine. Heat over low heat until heated through, about 5 more minutes.
⅔ cup heavy whipping cream
Taste and season with salt and pepper, if needed. Top with croutons and addional dollops of pesto, if desired.