Holliday was officially organized near Holliday Creek in 1890, when the city was platted, the Wichita Valley Railway was built through the area, and a post office was established. That same year, Maggie Elizabeth Holt and H.W. Simpson were married in Archer County. Their son, Herod Michael Simpson, was born on August 1, 1892. In 1894, H.W. Simpson left with a crew to drive cattle to Dodge City, Kansas, and was never heard from again. Maggie Simpson remained in Holliday, where she purchased a hotel in 1907 and owned and managed it until her death on June 18, 1946. Herod M. Simpson died on January 23, 1963. Both were interred at Holliday Cemetery.