Earliest visitors to the region now know as Winfield were bands of Chickasaw Indians who frequented this area as a hunting ground. The abundant wildlife of the Appalachian foothills made this area attractive to early hunters. After the Chickasaw Indians ceded their lands to the U S Government in 1816, settlers from the first colonies began moving west into the newly organized territory. These pioneers took advantage of the rich soil they found and farmed the land to sustain their families. In the post Civil War years, there was little opportunity for growth in the sparsely populated farmlands and underdeveloped wilderness of this area. Transformation began in 1896 with the arrival of surveyors of the Kansas City, Memphis, and Birmingham Railroad. They sought to link their cities by rail. As the little railroad village began to grow, residents decided their new hometown needed a name. Luxapillia was the first consideration, but some citizens jokingly began calling it "Needmore". The US Postal Service did not approve the new name because another Needmore already existed in Alabama.
Admirers of General Winfield Scott, a military leader in the Mexican War of 1847, suggested that the new town be named after their respected hero. Therefore on January 15, 1891, the town of Winfield was incorporated. As the railroad company laid out Winfield's first streets, they also launched the economy of the town. Through the years, the railroad brought in growth in commerce, new families, and even a famous visitor in 1934, President Franklin Roosevelt. The 1950's and 1960's ushered in an industrial age. The city prospered as roads were built and improved. A city school system was established in 1955, which has consistently been a top ranked system since its inception. Late September brings many visitors to Winfield for the annual Mule Day Festival, a tradition hosted by the Winfield Chamber of Commerce since 1975