The Skidmore Academy District is the oldest residential area in Ashland.

The varied building styles convey the cyclical intervals of growth and decline associated with Ashland during the period of historic significance (1871-1949). These eras include the population increase associated with the railroad's arrival in the late 19th century, the boom created by the orchard industry during the first decade of the 20th century, the post-World War I development preceding the Great Depression, and the increased residential density that followed World War II.

Adapted from the NRHP nomination submitted in 1992.

Ashland Academy was founded in 1872 with Reverend Joseph Henry Skidmore as president. It was located on North Main between South Laurel and Manzanita where the Briscoe Elementary School is now located. (The Briscoe school closed in 2004.)

The name of the school was changed frequently: Ashland Academy and Commercial College (1878), Ashland College and Normal School (1882), Ashland State Normal School (1887), and Southern Oregon State Normal School (1895).

In the 1890s, the school relocated to new quarters on Siskiyou Boulevard at Normal Avenue. In 1926, the school became Southern Oregon University.