The city of Anna has been proud of her public schools. The first schoolhouse, built in 1854, on the corner of Franklin and Monroe Street, was destroyed by fire. The city then built a frame schoolhouse on Lot 28, donated by Winstead Davie, and adjoining the fair grounds around 1860. In this building, the youth of the city were educated from 1860 to 1870, under the instruction of Mr. Young, Mr. Congor, William Cochran, E. Babcock, J. M. Brisbin, John Green, C. L. Brooks, H. Andrews, A. Inman, W. H. Hubbell and J. H. Sanborn. In 1869 the city felt the need for a new building and larger accommodations. The district directors C. W. Wilcox, Cyrus Shick and L. P. Wilcox, issued the necessary bonds. As a result, an elegant three-story brick edifice was built on Lot 23 in the northwestern part of town, at a total cost of $22,500 including furniture.
On Wednesday, January 5, 1870, the total enrollment of 126 children was moved from the small frame building to the new school, where the number was increased to 237 pupils, with J. H. Sanborn as Principal in charge.