Fiske was born in Harrison, New York, an affluent suburb in Westchester County just thirty minutes from New York City. The second of three sons of the wealthy hotel owner Lyman Fiske and his wife Jennie Maria (Durfee) Fiske, both of seventeenth-century Massachusetts descent, Fiske was still a young boy when his family moved into New York City, and he maintained a strong identity as a New Yorker for much of his life. As a young boy, Fiske was educated by private tutors and showed a strong interest in the arts. He recalled being taken to see his first play at Barnum's Museum at an early age and afterwards receiving the gift of a puppet theatre from his father. Later, whilst attending Mrs. Vanderhoff's School he became exposed to Shakespeare through dramatic readings given by the headmistress's husband. Likewise, he had also been giving a small printing press and, as a boy, he had begun printing his own monthly paper. Fiske next enrolled at Dr. Chapin's Collegiate School for Boys, a college preparatory school on Madison Avenue where he continued to pursue writing. Upon finishing there, he traveled for a summer in Europe and then entered New York University in 1878. There he was asked to sign a pledge to forsake dens of iniquity like theaters, taverns, dance halls, and billiard rooms. Fiske subsequently admitted that he and his friends kept their fingers crossed when it came to attending theaters.