J. O. Cole wanted his grandson to become a lawyer, and with that in mind, sent him to Worcester Academy in Massachusetts in 1905. Porter brought an upright piano with him to school and found that music, and his ability to entertain, made it easy for him to make friends. Porter did well in school and rarely came home to visit. He became class valedictorian and was rewarded by his grandfather with a tour of France, Switzerland and Germany. Entering Yale College in 1909, Porter majored in English, minored in music, and also studied French. He was a member of Scroll and Key and Delta Kappa Epsilon fraternity, and contributed to campus humor magazine "The Yale Record". He was an early member of the Whiffenpoofs "a cappella" singing group and participated in several other music clubs; in his senior year, he was elected president of the Yale Glee Club and was its principal soloist.