Winstead Davie School Inn During the year 1853, Winstead Davie, who owned most of the land which is now the site of the City of Anna and Col. Lewis W. Ashley, Division Engineer, who had come into possession of a portion of the same tract, determined to lay out a town at this point. The proper surveys were made by Francis H. Brown, the County Surveyor, and lots were laid out on both sides of Main Street and the railroad. Mr. Davie decided to name the town in honor of his beloved wife Anna and under this name the plat was entered upon the county records on March 3, 1854. The Davie School Inn Bed and Breakfast was once a public school named after the founder of Anna, Winstead Davie. The Davie School Inn was stared in 2004, the Winstead Davie School was built in 1910. Anna, IL takes pride in its history and of its largest bed and breakfast in Illinois.