The development of Ashland that began with the discovery of gold near the present site of Jacksonville in early 1852, and the Donation Land Claim Act of 1850, sparked the settlement of this area.

The anticipation of the arrival of the railroad instigated a major wave of building and the platting of this section of Ashland when it was sold to the Oregon and California Railroad Company in 1873. The railroad company surveyed this major addition that doubled Ashland's size.

The first train pulled into Ashland in 1884. Residences and commercial structures were constructed during 1884-88. The Depot Hotel was built in 1888. By 1890, lodging houses, saloons, restaurants, stores and warehouses formed a separate commercial district on A Street where residents could conveniently purchase goods and services, developing the Railroad Addition as a self-contained unit.

In 1893, the national depression slowed building in this district, but as railroad business increased in 1898, the second major period of growth began.

As railroad workers and tradespeople moved into the area after 1900, one or one-and-one-half story vernacular frame houses were being constructed which provided affordable housing for the brakemen, firemen, and conductors, as well as carpenters, barbers,

The relatively small number of new buildings constructed in the railroad district during 1913 and 1930 reflects the city's absorption in World War I, a slowing economy, and the opening of the Southern Pacific Natron Cutoff in 1927 which bypassed Ashland.

With the Great Depression, many people lost their homes. Renters, retirees, and those on stable or subsidized incomes increasingly occupied the Railroad Addition. Many dwellings were converted to multi-family use. New building was scarce.

Adapted from the NRHP nomination submitted in 1999.

This 1,170-acre historic district contains 256 contributing buildings.