Caldwell began in 1871 as a trading post on the Chisholm Trail.  Cowboys heading North and South stopped here to buy provisions before continuing on their journey. 
Cowboys, weary after long cattle drives through Indian Territory, could find a haven for entertainment and excitement in the town known as "The Border Queen."  Caldwell began to boom in the 1800's with the arrival of the first railroad in the area.  It soon grew into wild and wooly cowtown, rivaling Abilene and Dodge City.  In 1893, when the Cherokee Strip was opened for settlement, Caldwell experienced another massive influx of settlers who thronged to the area for preparation for the run.  The fertile soil of the area enticed many of the families to stay in the community and make their homes rather than facing other unknowns in the territory to the south.  Today, Sumner County, where Caldwell is located, has the distinction of being the largest winter wheat-producing county in the nation.