Harry Leith Ross was born on January 27, 1886 in Mauritius, an island nation in the Indian Ocean. His love of art was fostered by his Dutch maternal relatives, Barbara van Houten and Hendrik Willem Mesdag, a well-known marine watercolorist, who were both respected and established artists. Lieth-Ross studied at the University of Birmingham in England for two years before coming to America at 17, when his parents sent him to New Mexico to work under his uncle as a paymaster. After three years failing to be a businessman he sought employment at the printing and engraving company Smith-Brooks, in Denver. He moved to Paris in 1908 where he studied at the Delecluse Academy and at the Acadeemie Julian with Jean Paul Laurens, and later learning landscape painting in England under Stanhope Forbes. Upon his return to the U.S. in 1910, he took classes with Charles Yardley Turner at the National Academy of Design in New York City before deciding to attend the Art Students League Summer School in Woodstock, New York, at the age of twenty-eight. He was inspired by the works of Birge Harrison, John F. Carlson, and John Fulton Folinsbee.