Oakley Hoopes Bailey (June 14, 1843 - August 13, 1947) was a prolific American viewmaker, artist, and lithographer active in late 18th and early 19th century. Bailey was born in Beloit, Mahoning County, Ohio. He matriculated in 1861 at Mount Union College in Alliance, Ohio. At the outbreak of the American Civil War he briefly abandoned his studied for 2 years, wherein he saw combat as a Union solider. After the war, in 1866, he returned to Mount Union to complete his degree. Bailey was the younger brother of another view artist, Howard Heston Bailey (1836 – 1878) and followed his brother into the print business, producing his first city views, of Milwaukee, Wisconsin, in 1871. Active from 1871 to1926, Bailey is known for more than 375 recorded city views, covering more than 13 states 2 Canadian provinces, making him one of the most active viewmakers in American history. In 1875, he settled in Cambridge, Massachusetts and most of his subsequent work focused on Massachusetts and Connecticut. Bailey worked with many other American viewmakers of the period, including his brother, Howard Heston Bailey, Thaddeus M. Flower, and J. C. Hazen, among others. Bailey died in his hometown of Alliance at the ripe old age of 103.