Local ranch hands looking for a way to settle bets on who was the best at various cowboy fundamentals, founded the world’s first Rodeo, July 4, 1869.

The following year the Kansas Pacific Railway built a station in what was to become Deer Trail and platted the town five years later. It soon became a shipping point for grain, livestock, and eggs.

Over the decades, Deer Trail has been devastated by several natural disasters. Even though it faced five severe snow events between 1876 and 1913, it incorporated in 1920. By the late 1920’s it had grown into a busy hub of commercial activity, with two banks, five grocery stores, and three hotels.

The Great Depression of the 1930’s had a very adverse impact on the economy of the area. Then, a huge flood in June of 1965 destroyed or severely damaged many businesses in its downtown area, most of which were never rebuilt.

In recent years the large Richmil "Open Space" area has been established, as well as a nearby auto racing track.

Today Deer Trail has a population of around 600, but is admired in the area for an indoor swimming pool within the local high school and a Pioneer Historical museum.​