In 1980, she earned a Bachelor of Arts from Radcliffe College at Harvard University. During college, Kennedy had "considered becoming a photojournalist, but soon realized she could never make her living observing other people because they were too busy watching her." After graduating, Kennedy was hired as a research assistant in the Film and Television Department of the Metropolitan Museum of Art in New York. She later became a "liaison officer between the museum staff and outside producers and directors shooting footage at the museum", helping coordinate the "Sesame Street" special "Don't Eat the Pictures". On December 4, 1984, Caroline was threatened when a man telephoned the museum and stated his name and address while reporting that a bomb had been planted there. Three days later, he was arrested for the threat. In 1988, she earned a Juris Doctor from Columbia Law School, graduating in the top ten percent of her class.