Settlers came to this locality in 1876. The county was organized in 1889. Pioneer school district no. 5 originated by court order in 1890 to serve this area with schools known as Tallahone, Poole, and Wayside, taught usually in homes. In 1914, Frederic Foster of New York gave this 2-acre school site to the county. The district bought materials, and patrons erected this 28 x 36-foot schoolhouse, painting it red. It soon became the focus for the community - site for elections, church services, and other activities, as well as housing the Wayside School. The trustees in 1914 were James A. Poole, J. M. Story, and Earl Talley.
Despite enrolment fluctuations caused by drouths, oil booms, and other economic factors, Wayside prided itself on scholastic excellence. Beginning in 1929, high school students were transferred by bus into Pampa, Wayside District paying their tuition. In 1933-1934, all grades were transferred - an arrangement used until 1950, when Wayside consolidated with Pampa.
White Deer Land Co., successor to original donor Frederic Foster, then deeded the red schoolhouse for continuing community use to trustees Paul Caylor, R. E. Montgomery, and J. T. Roberts. Current trustees are C. W. Osborne, J. T. Rogers, and Jack Sloan.