Kennedy graduated from the private St. Albans School, in Washington, D.C.. After completing a Bachelor of Arts degree at Wesleyan University, in Middletown, Connecticut, in 1984, he continued his studies at Yale University, in New Haven, Connecticut, earning a master's degree from the School of Forestry and Environmental Studies. He then attended the University of Connecticut School of Law at night, earning a Juris Doctor degree. On May 19, 2013, Kennedy received an honorary Doctor of Laws degree from the University of New Haven.