While studying Persian, Fiske came across some stories about chess, a game he may have played in college. He joined the New York Chess Club in 1856. He began collecting books about chess, and in January 1857, he founded and began editing The American Chess Monthly, with the famous chess player, Paul Morphy, as associate editor. Later that fall, Fiske organized the first American Chess Congress in New York, and published The Book of the First American Chess Congress, a volume about the Congress and the history of chess. Later in his life, Fiske would encourage the game of chess in Iceland, supporting the Reykjavík Chess Club, starting a chess magazine printed in Iceland (Í Uppnámi), and printing a number of pamphlets about the game for free distribution in Iceland. He provided chess sets and books to the inhabitants of the residents of the island of Grímsey. His Chess in Iceland and in Icelandic Literature was published posthumously, and he willed his collection on chess to the National Library of Iceland.