Oakley was originally known as "Four Mile," because it was a popular stop in the mid-1800s for wagons on the Madison Turnpike, now Madison Road.
The land was purchased in 1846 by Anthony Brown, and in 1853, Paul Shuster bought 34 acres and named it Oakley because of the many oak trees. The villagers, however, called it Shusterville. The railroad came through in 1857. The village officially registered its name as Oakley in 1869.
During the 1890s, the community began to grow, and the famous Oakley Race Course for thoroughbred racing opened. The race track closed a few years later due to a state law prohibiting betting. The village incorporated in 1898.
The Cincinnati Milling Machine Company incorporated in 1889, and by 1905 it had moved to Oakley along the railroad. Soon the old race track property was covered in new homes for the factory workers.
Library service began in 1910, when a deposit station opened in Barton's Drug Store. A full-service branch opened in 1926 in rented quarters near what is now the 20th Century Theater. In 1940, a permanent branch library was established at the corner of Gilmore and Madison Road and served the community until 1986. A new building was constructed and dedicated in 1989.
Oakley was annexed to the city of Cincinnati in 1913. In the same year, Aglamesis Bros. Ice Cream Parlor and Candy Shoppe opened to accommodate the growing population of workers at the Mill, as the Cincinnati Milling Machine Company was called.
During World War I, the Mill was a major producer of weapons of war. Sales declined after the war, but the company bounced back in the 1930s to become the country's largest producer of machine tools. This trend continued through subsequent American wars. and in 1970, the company changed its name to Cincinnati Milacron, Inc.
Although Milacron continues to operate in multiple locations worldwide, the Oakley factories are no longer running. The Oakley retail development Center of Cincinnati is located on the former Milacron factory property.
Oakley Square on Madison Avenue is the heart of Oakley. In 1927 and 1932, small parcels of land were acquired and turned into green space on the square, called the Geier Esplanade. During the 1930s and 1940s, streetcars came every 5 minutes to Oakley Square.
The 20th Century Theater was built in 1941 and is a distinctive Oakley landmark with its 72-foot tower rising over the business district. The deteriorating Art Moderne theater was slated for demolition in the early 1990s, but was spared due to its historical significance and is finding a new life as a concert and special events venue.
Oakley History (cincinnati.com article)