Formal frontier education appears to have begun in this region around the late 1820s or early 1830s. At that time, instructor R.B. Kendall was just a child, and he later recounted that he attended school at the McGahan log house, which was located on Pennsylvania Avenue, near Main Street and the river. The school was privately funded by the parents of the schoolchildren, as was the custom on the western frontier.
The first proper schoolhouse appears to have been established in 1835 in a log cabin on the western end of State Avenue near Watson Street. This would later be the location of the J.K. Jolly house and after that the M.M. Watson house. It was a modest cabin with a single dim window covered in waxed paper, a clapboard roof held down by logs, and a primitive wood-burning opening for heat. No iron work or even nails were used its construction. The desks were simple pine boards held up by stakes. Students were instructed by Mr. John Byers and R.B. Kendall.
After the log school was torn down, a subscription school was established beside the First Baptist Church where the old Ferree homestead was. It was also a log building, but it was built 4-5 feet off the ground. The space below the floor was used to store wood, and to punish the occasional disruptive pupil. The teacher was Ebeneezer Riddle, and the attendance fee per pupil was $1.00-$1.50 per month. Students attended 9-4 daily without recess, and even went to school on Saturdays. School term lasted 6-7 months with summers off. Examinations were held by Squire Cooper periodically, several miles away.
From approximately 1840 through 1857, a school for all of Moon Township was established on the property of Samuel Neely (5th Avenue on the west side of Main Street). It was a brick building, and the teachers were R. B. Kendall and Charles Meegan. However, when 5th Avenue was built, the school was forced to relocate.
Middletown then built a school 150 feet south of 5th Avenue, at the corner of Main Street and Oak Way. This frame building, which later became the home of J.E. Helm, housed up to 30 pupils. The teachers were Miss Irene Dillon, Mr. Whitmore, Mr. James A. Watt, Miss Hattie Dickson, Jack Phillips, William Verner, Miss Mollie Harbison, Miss Sarah Getty, Mr. Scott McCormich, and Mr. Samuel Guy. Eventually, the small school faced overcrowding, and, in 1873, Reverend Josiah Dillon donated a small building on State Avenue to supplement the school. However, by 1885 the school had outgrown these facilities as well.
It was the end of an era. Middletown would cease to exist within the next year, replaced by a new modern town with and brand new modern school to go with it. The frontier school days had come to an end, and a new progressive history was about to emerge, bringing with it expansion and innovation.