Bands of Chickasaw Indians were the earliest known visitors to the region now known as Winfield, using the wildlife-rich Appalachian foothills as a hunting ground. After the Chickasaw ceded their lands to the U.S. Government in 1816, settlers from the first colonies moved west into the newly organized territory and farmed the rich soil to sustain their families. In the post Civil War years, the area remained sparsely populated farmland and underdeveloped wilderness with little opportunity for growth. Change began with the arrival of surveyors for the Kansas City, Memphis, and Birmingham Railroad, who sought to link their cities by rail, and the small railroad village started to grow. Residents considered naming the new town Luxapalilla, but some jokingly called it Needmore, a name the U.S. Postal Service rejected because another Needmore already existed in Alabama. Admirers of General Winfield Scott, a military leader in the Mexican War of 1847, proposed naming the town after him, and Winfield was incorporated on January 15, 1891. As the railroad company laid out the town's first streets, it also launched the local economy. Over the years, the railroad brought growth in commerce, new families, and a visit in 1934 from President Franklin Roosevelt. The 1950's and 1960's brought an industrial age, and the city prospered as roads were built and improved. A city school system established in 1955 has remained top ranked since its beginning, and since 1975 the annual Mule Day Festival hosted by the Winfield Chamber of Commerce has drawn many visitors each late September.