An American original, Shepherd pursued his own pathway amidst the strong influences of new musical languages of the first half of the twentieth century, preferring "the necessary inevitable beauty of the simpler euphonies" (from a letter to Percy Goetschius, 1934). But within this traditional propensity, he nevertheless inclined toward a unique take on modality, chromaticism, the use of folk tunes, and other time-honored techniques and materials. From 1892 - 1897, he studied at the New England Conservatory with Goetschius and Chadwick, absorbing the Classical tradition as well as becoming acquainted with the changing musical scene influenced by Wagner, Brahms, and the modern French composers. From 1898 to 1909, he worked as a conductor, pianist and composer in Salt Lake City, and established a branch of the American Music Society there. During this period, Shepherd composed an orchestral work, the Overture joyeuse, Op. 3 (1901), and his First Pianoforte Sonata, Op. 4 (1907), notable for its folk tune-like melodies, presumably influenced by the nationalistic values of the Society. The impressive songs The Lost Child (with words by J.R. Lowell) and Sun Down (to words by W.E. Henley) were completed respectively in 1908 and 1909, toward the end of his stay. Shepherd returned to Boston to teach at the New England Conservatory from 1909 - 1920, a job that was interrupted by a year's stint in the military in France in 1918 - 1919. This was an especially productive period for him and he began to receive more recognition for his work, being cited as "one of the most keenly individualized of American composers, and one of the most daring in the employment of ultra-modern resources" (A. Farwell and W.D. Darby, Music in America, 1915). His works at this time include the orchestral Overture to a Drama (1919), a Violin Sonata (1918), The City in the Sea for baritone, double chorus, and orchestra (1913), and the song The Gentle Lady (setting words by J. Masefield, 1915). In 1920, Shepherd moved to Cleveland to serve as the assistant conductor (1920 - 1926) and program annotator (1920 - 1930) for the newly formed Cleveland Orchestra. He was also employed as a critic (1928 - 1931), and began a long-term association with the Western Reserve University as a professor. Although these activities required a good deal of his time, he was able to create several works: a grand-scale development of melodies derived from American folk song with strong rhythmic underscoring, the Horizons (Symphony No. 1) (1927), the Symphony No. 2 (1938), a Fantasy on Down East Spirituals (1946), and a Violin Concerto (1946). His Second Piano Sonata (1930) contains many Celtic themes, expanded in an abandoned Romantic style with modal but dissonant harmonies. His Piano Quintet in F sharp Minor (1940) features dramatic chromaticism. Despite a hearing problem, he continued to compose significant works after 1950, notably the String Quartet No. 4 (1955) and the song Sarasvati (1957).