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Winfield originally tried to become an incorporated village in 1884 under the town name 'Frederick Park.' However, the motion was denied as the town did not have 300 residents as was required for incorporation. When the village was finally incorporated in 1921, the town had a population of 310 people. The earliest settlers, Erastus and Jude P. Gary came to Winfield in 1832. Winfield was originally known as Gary's Mill after these early settlers, and later, Fredricksburg, owing to a significant German-speaking population.