Directions

1. In a large bowl, whisk together vinegar, oil, salt, and pepper; set aside. Fill a large bowl halfway with ice water; set aside.
2. Trim off stem end of tomatoes. Carefully drop tomatoes and garlic into a large pot of boiling water; cook 1 to 2 minutes. Use a slotted spoon to transfer tomatoes and garlic to ice water; use a knife to peel garlic and tomatoes. Cut tomatoes in half lengthwise; scoop out seeds with fingers. Add garlic and tomatoes to dressing; toss. Use a slotted spoon to transfer tomatoes and garlic (keeping them separated and in a single layer) to a shallow 11x16-inch baking pan; set aside remaining dressing.
3. Bake in a 300 degree F oven, wrapping garlic in foil after 2 hours. Continue baking until tomatoes are leathery and slightly caramelized, about 1/2 hour more. Cool 5 minutes. Remove garlic from foil. Use a metal spatula to transfer tomatoes and garlic to a serving dish; drizzle with enough dressing to lightly coat. Refrigerate leftover dressing for another use.