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Prepare the baking dish. Preheat oven to 400 F. Place tomatoes in a large baking dish with deep sides. Add 2 heads of garlic, cut side up, as well as 1 shallots. Just nestle them in there.
Assemble the tomatoes. Cover with olive oil, making sure to almost reach the tops of the tomatoes (you may need more olive oil depending on the size of your baking dish). Sprinkle with 1 tsp kosher salt and ¼ tsp black pepper, then top with fresh herbs. No need to push herbs down into olive oil, they can rest on top.
Cook, then serve. Roast for 1 hour, or until garlic and shallots have become soft and sweet, and the tomatoes have browned on top and begin bursting. Let cool slightly. Gently squeeze garlic cloves out of peel and into the tomatoes and oil, discarding the skin. Serve with crusty bread, crackers, fresh cheese, Italian meats - the possibilities are endless!