Yates was brought up in the mid-western countryside, an environment which was an important factor in his later development as a landscape artist. He spent the summer of 1894 at Chase's Shinecock Hills Summer School. His mother accompanied him there and she served meals to the students for extra income. That fall Cullen, his mother, and brother Roland set sail for Paris. Yates enrolled at the Academie Julian for day classes and at the Academie Colorossi for evening classes. The next summer Yates went to Barbizon with Howard Hildebrandt and other American artists to paint. The spring of 1896 was spent in the chateau region of France teaching painting to American students. Returning to New York in 1897, Yates had difficulties establishing himself as an artist and so returned to Ohio where he taught at the Cleveland School of Art.
Yates returned to New York in 1900 and shared an apartment part-time with Leonard Ochtman. That summer and the next Yates went to Old Lyme, Connecticut with Allen B. Talcott, Will Howe Foote and Clark Vorhees; they stayed at Florence Griswold's boarding house. In 1902 Yates exhibited 14 pictures at the National Academy as part of a group of Old Lyme painters. His work began to be accepted at juried exhibitions and soon he was winning major awards.
The next several summers were spent at Cape Ann at Gloucester, Mass. Around 1905 he began spending summers in the Poconos and painting the landscape around the Delaware River Gap. Around 1909 he began spending summers along the Maine coast. In 1910 on a painting trip to Ogunquit, Maine he met Mabel Taylor of Baltimore, whom he married the following year. Her parents had a summer home there. In 1912 he built a summer cottage in Shawnee-on-the-Delaware, PA where he had acquired land from the industrialist Charles Worthington who traded Yates the land for a large painting. Yates maintained a studio at the Van Dyke Building in New York where he would work up paintings from sketches he had made during the summer. He would paint in the spring and fall in Pennsylvania, summers in Ogunquit, and winters in New York. He had a one man show at the Arlington Galleries in 1921. In 1923 the couple winterized their home in Shawnee and moved there permanently.
