Kittitas was constructed as part of the westward expansion of the Chicago, Milwaukee, St. Paul, and Pacific Railroad, the Kittitas Yard and Depot Became the center of the community of Kittitas: one of the many small, agricultural towns that sprang up along the railroad lines. The railroad linked Kittitas to other small communities and the rest of the country, providing farmers and business people a way to sell their products in other towns and cities.

A post office, general merchandise and drug store, a Baptist Church, agricultural warehouses, and other small businesses were built around the small depot. Along with the depot, the Kittitas Yard included storage and maintenance buildings, a water tower, and other structures necessary for the maintenance of a major transcontinental railroad.
The depot is the only significant structure sill intact at the Kittitas Yard. It is an excellent example of turn-of-the-century railroad architecture, and as such was placed on the National Register of Historic Places in 1992. The depot is owned and managed by the Washington State Parks and Recreation Commission.

The Milwaukee Road, the popular name for the Chicago, Milwaukee, St. Paul, and Pacific Railroad, was founded in 1847 to serve the area from Mississippi to Wisconsin. Within 50 years, it became one of the most prosperous railroads in the country.
In 1905, Milwaukee Road officials began expanding west, running lines from Chicago to Seattle. At the same time, they decided to electrify the lines through the western mountains, to increase operating efficiency.
Despite the increased efficiency, the financial stability of the railroad began to crumble, prompted by the high cost of the western expansion, electrical expenses, and competition with other railroads and ships using the newly-opened Panama Canal. In 1980, the last Milwaukee train traveled over the Cascades and thereafter the system served only the Midwest.

The Milwaukee Road once served as a vital link, providing economic and social connections between small, scattered communities in Washington. Today, it is once more a link between these many communities though rather than riding the rails, people now hike, bike, or ride horses along this route.
Stretching more than 250 miles from Cedar Falls near North Bent to Tekos at the Idaho Border, the John Wayne Pioneer Trail passes through tunnels, over mountains, along rivers and lakes, and through dry, sagebrush countryside.