Nicknamed "Rym," Berry attended Cornell University, graduating in 1904 and earning a law degree in 1906.
During his senior year, Berry was elected to the Sphinx Head Society and editor of the Cornell Widow with George Jean Nathan as business manager.
During these years, Berry also served as graduate manager of the Cornell University Glee Club.
In 1932, he was president of the Eastern Collegiate Baseball League, and he was named to the American Olympic Committee in 1938.
His pieces for the Ithaca Journal ran under the heading "State and Tioga" from 1931 to 1956 and reflected his gentle humor and wry observations about rural life and human nature.