This collection is comprised of 14 illustrated letters that Henry Brevoort Eddy of Mamaroneck, New York, wrote to Louise Lyman, a friend living in Tarrytown, New York, and London, England. Eddy wrote 4 letters from New York City and Tuxedo Park, New York, between July and September 1895; he discussed a heat wave affecting Tuxedo Park and the surrounding area, as well as Sunday excursions in New York City, illustrated with cartoon portraits of beachgoers and a ferry boat. While in Tuxedo Park, he wrote of and illustrated sporting activities such as golf, bicycle riding, and tennis. A humorous drawing in his letter of August 12, 1895, shows a man and a woman quivering after a loud burst of thunder. In his other undated letters, he described and illustrated aspects of his social life and leisure activities, which included his frequent attendance at the Harvard Club in New York City. He often wrote his letters on Harvard Club stationery.
Eddy shared his observations on topics such as the effects of bicycling on women and commented on Lyman's letters and letter-writing habits. He occasionally mentioned his artistic work, including his upcoming posters for the New York Ledger and his desire to make his living drawing cartoons. Accompanying illustrations depict Eddy and others reading, and include several sketched cartoon portraits. Many of Eddy's drawings and observations were humorous, and on one occasion his work prompted him to depict himself as the devil drawing cartoons. Two illustrations show men fighting, and 3 refer to "Carl," an African-American acquaintance. One letter dated "July 8" includes a newspaper clipping of a poem Eddy composed, illustrated with several small, refined drawings and titled "This Is the House That Jack Built."