[3][4] In 1902, Dickey and his mother, also an avid naturalist, joined a Sierra Club group hiking King's River Cañon and climbing Mount Whitney.

Others on this trip included John Muir, C. Hart Merriam, Dr. Henry Gannett, historian Theodore Hittell and landscape artist William Keith.

[6] During his senior year at Yale, Dickey suffered severe heart failure; he slowly recovered his health during a three-year convalescence, living for a time first in Ojai[5] and later at his parents' home in Pasadena.

Dickey married Florence Van Vechten on June 15, 1921, and became active in community and business affairs, serving as a trustee of the Southwest Museum, Los Angeles (1920–1928), and President of the Board of Pasadena Hospital (1924–1925),[3] and as a director of the Pasadena branch of the Pacific Southwest Trust & Savings Bank (1924–29).

[7] Upon recovering his health, Dickey began to pursue his interests in natural history by photographing and collecting birds and small mammals.